Dichloromethane → HCID 54394052, compound

HRID 233756Notes

Reaction equation

HRID 233756 reaction equation
[CH2:1]([C:8]1[N:9]=[C:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[C:16]3[CH2:22][C@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2C(OCC2C=CC=CC=2)=[O:29])[S:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl>CO>[OH-:29].[NH4+:9].[CH2:1]([C:8]1[N:9]=[C:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[C:16]3[CH2:22][C@H:23]2[CH2:27][CH2:26][CH2:25][NH:24]2)[S:11][CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 22868967HCID 22868967, compound

Product 2

HCID 14923Ammonium HydroxideHCID 54394052HCID 54394052, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

(R)-5-(4-Benzyl-1,3-thiazol-2-yl)-3-(N-benzyloxycarbonylpyrrolidin-2-yl-methyl)-1H-indole was used, and the reaction was heated at 40° C. for 24 hours. Chromatography using methylene chloride:methanol:ammonium hydroxide [9:1:0.1] afforded the title compound (12%) as an amorphous solid: 1H NMR (CDCl3) δ 9.1 (br s, indole NH), 8.17 (d, J=1.4 Hz, 1H), 7.74 (dd, J=1.6 and 8.5 Hz, 1H), 7.35-7.21 (m, 6H), 7.02 (s, 1H), 6.67 (s, 1H), 4.22 (s, 2H), 3.5 (br s, NH), 3.41-3.29 (m, 1H), 3.03-2.73 (m, 4H), 1.94-1.61 (m, 3H), 1.49-1.38 (m, 1H); 13C NMR (CDCl3)δ 169.9, 157.0, 139.2, 137.4, 129.2, 128.5, 127.7, 126.4, 125.5, 123.8, 121.2, 117.3, 114.3, 113.3, 111.7, 59.2, 46.0, 38.1, 31.5, 31.1, 24.9; HRMS calculated for C23H23N3S 374.1615, found 374.1691.

Sources & evidence

ORD record
ord-5d8a297126624d4e83127a049d192ba7
Source dataset
uspto-grants-1997_01
Patent number
US05594014

Reaction notes

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