Sulfanilamide Hydrochloride → HCID 178450648, compound

HRID 2213269Notes

Reaction equation

HRID 2213269 reaction equation
C(OC(C1C=C2C(=CC=1)NC(=O)C2)=O)C(C)C.CN(C=C1C2C(=CC(CO[Si](C(C)(C)C)(C)C)=CC=2)NC1=O)C.[CH2:41]([O:45][C:46]([C:48]1[CH:49]=[C:50]2[C:54](=[CH:55][CH:56]=1)[NH:53][C:52](=[O:57])[C:51]2=[CH:58][N:59]([CH3:61])C)=[O:47])[CH:42]([CH3:44])[CH3:43].Cl.NC1[CH:69]=[CH:68][C:67]([S:70]([NH2:73])(=[O:72])=[O:71])=[CH:66][CH:65]=1>>[CH2:41]([O:45][C:46]([C:48]1[CH:49]=[C:50]2[C:54](=[CH:55][CH:56]=1)[NH:53][C:52](=[O:57])[C:51]2=[CH:58][NH:59][C:61]1[CH:69]=[CH:68][C:67]([S:70](=[O:72])(=[O:71])[NH2:73])=[CH:66][CH:65]=1)=[O:47])[CH:42]([CH3:43])[CH3:44]

Participants

5

Reactant 4

HCID 80197Sulfanilamide HydrochlorideHCID 541641603-Dimethylaminomethylene-6-(t-butyldimethylsilyloxy)methyl-1,3-dihydro-indol-2-oneHCID 541859042-oxo-2,3-dihydro-1H-indole-5-carboxylic acid isobutyl esterHCID 544018903-[(dimethylamino)methylene]-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid isobutyl ester

Product 1

HCID 178450648HCID 178450648, compoundYield 66%

Procedure

3-Methylthio-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid isobutyl ester was prepared in 59% yield from isobutyl 4-aminobenzoate according to Procedure D: 1H NMR (DMSO-d6): δ 0.93 (d, J=6.6 Hz, 6H), 1.93 (s, 3H), 1.98 (septet, J=6.6 Hz, 1H), 4.02 (m, 2H), 4.62 (s, 1H), 6.92 (d, J=8.2 Hz, 1H), 7.79 (s, J=1H), 7.86 (d, J=8.2 Hz, 1H), 10.91 (s, 1H); ESI-MS m/z 302 (M+23)−. Zinc reduction of 3-methylthio-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid isobutyl ester according to Procedure δ provided 2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid isobutyl ester in 99% yield: 1H NMR (DMSO-d6): δ 0.93 (d, J=6.6 Hz, 6H), 1.97 (septet, J=6.6 Hz, 1H), 3.53 (s, 2H), 3.99 (d, J=6.6 Hz, 2H), 6.88 (d, J=8.2 Hz, 1H), 7.75 (s, J=1H), 7.82 (d, J=8.2 Hz, 1H), 10.72 (s, 1H); ESI-MS m/z 256 (M+23)+. Conversion of 2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid isobutyl ester to 3-[(dimethylamino)methylene]-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid isobutyl ester (mixture of E and Z isomers) was accomplished in 75% yield according to Procedure G: 1H NMR (DMSO-d6): δ 0.94 Z (d, J=8.8 Hz, 6H), 0.94 E (d, J=8.8 Hz, 6H), 1.94–2.01 Z and E (m, 2H), 3.30 Z (s, 6H), 3.32 E (s, 6H), 3.97–3.99 Z and E (m, 4H), 6.75 Z (d, J=8.2 Hz, 1H), 6.83 E (d, J=8.2 Hz, 1H), 7.47 E (s, 1H), 7.53 Z (d, J=0.8.2 Hz, 1H), 7.59 E (d, J=8.2 Hz, 1H), 7.73 Z (s, 1H), 7.88 Z (s, 1H), 7.98 E (s, 1H), 10.34 Z (bs, 1H), 10.44 E (bs, 1H); ESI-MS m/z 289 (M+1)+. The title compound was prepared in 66% yield from 3-[(dimethylamino)methylene]-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid isobutyl ester and 4-aminobenzenesulfonamide hydrochloride according to Procedure J: 1H NMR (DMSO-d6): δ 0.96 (d, J=6.6 Hz, 6H), 2.01 (septet, J=6.6 Hz, 1H), 4.04 (d, J=6.6 Hz, 2H), 6.93 (d, J=8.2 Hz, 1H), 7.26 (s, 2H), 7.60 (d, J=8.7 Hz, 2H), 7.71 (dd, J=1.6, 8.2 Hz, 1H), 7.76 (d, J=8.7 Hz, 2H), 8.27 (s, 1H), 8.86 (d, J=12.5 Hz, 1H), 10.83 (d, J=12.5 Hz, 1H), 10.95 (s, 1H); APCI-MS m/z 414 (M−H)−. Anal. Calcd for C2H21N3O5S: C, 57.82, H, 5.09; N, 10.11; S, 7.72. Found C, 57.91, H, 5.16; N, 10.02; S, 7.65.

Sources & evidence

ORD record
ord-542a831dc2d24e6f897b238990b1ad31
Source dataset
uspto-grants-2006_09
Patent number
US07105529B2

Reaction notes

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