Trifluoroacetic anhydride → HCID 178478618, compound

HRID 849409Notes

Reaction equation

HRID 849409 reaction equation
[ClH:1].Br[C:3]1[CH:4]=[CH:5][C:6]2[N:12]([CH2:13][C:14]3[N:15]=[CH:16][NH:17][CH:18]=3)[CH2:11][CH2:10][N:9]([C:19]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)C=CC=3)=[O:20])[CH2:8][C:7]=2[CH:31]=1.C(C(O)=O)(=[O:39])C1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(C1C=CC2[N:67](CC3N=CN(C(OC(C)(C)C)=O)C=3)[CH2:66][C@@H:65]([CH2:81][C:82]3[CH:87]=CC=CC=3)N(S(C)(=O)=O)CC=2C=1)#N>CN(C=O)C.C(Cl)Cl>[ClH:1].[ClH:1].[ClH:1].[NH:17]1[CH:18]=[C:14]([CH2:13][N:12]2[C:6]3[CH:5]=[CH:4][C:3]([C:81]4[CH:65]=[CH:66][N:67]=[CH:87][CH:82]=4)=[CH:31][C:7]=3[CH2:8][N:9]([C:19](=[O:20])[C:21]([C:30]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:39])[CH2:10][CH2:11]2)[N:15]=[CH:16]1

Participants

7

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 11915Phenylglyoxylic AcidHCID 69841490(R)-7-cyano-2,3,4,5-tetrahydro-1-[(((1,1-dimethylethoxy)-carbonyl)-1H-imidazol-4-yl)methyl]-4-(methylsulfonyl)-3-(phenylmethyl)-1H-1,4-benzodiazepineHCID 1784796677-Bromo-2,3,4,5-tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-1H-1,4-benzodiazepine, hydrochloride2×

Product 1

HCID 178478618HCID 178478618, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Example 297 was prepared as a yellow solid from 7-bromo-1,4-benzodiazepine (see Example 11) and benzoylformic acid by the following sequence: Example 252, in 10:1 methylene chloride:DMF and with chromatography with 50% EtOAc/hexanes; treatment with trifluoracetic anhydride and workup as described in Compound A of Example 296; Compounds B, C and D of Example 296. M+H (438).

Sources & evidence

ORD record
ord-13b4bbc25bfa4396bc3a4642ee01562c
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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