Trifluoroacetic acid → [3-[3-(4-fluoro-phenyl)-4H,6H-1,2,5,10b-tetraaza-benzo[e]azulen-5-yl]-3-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic Acid tert-butyl ester

HRID 1253901Notes

Reaction equation

HRID 1253901 reaction equation
C(O[C:6]([N:8]1[CH2:17][C:16]2[N:12]([N:13]=[N:14][C:15]=2[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[C:11]2[CH:25]=[CH:26][CH:27]=[CH:28][C:10]=2[CH2:9]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.[C:36]([O:40][C:41]([NH:43][C@H:44]([CH2:49][C:50]1[CH:55]=[C:54]([F:56])[C:53]([F:57])=[CH:52][C:51]=1[F:58])[CH2:45]C(O)=O)=[O:42])([CH3:39])([CH3:38])[CH3:37].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)CCl>[C:36]([O:40][C:41](=[O:42])[NH:43][CH:44]([CH2:49][C:50]1[CH:55]=[C:54]([F:56])[C:53]([F:57])=[CH:52][C:51]=1[F:58])[CH2:45][C:6]([N:8]1[CH2:17][C:16]2[N:12]([N:13]=[N:14][C:15]=2[C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[C:11]2[CH:25]=[CH:26][CH:27]=[CH:28][C:10]=2[CH2:9]1)=[O:7])([CH3:37])([CH3:38])[CH3:39]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7146288(R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acidHCID 687803143-(4-fluoro-phenyl)-4H,6H-1,2,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester

Product 1

HCID 68782199[3-[3-(4-fluoro-phenyl)-4H,6H-1,2,5,10b-tetraaza-benzo[e]azulen-5-yl]-3-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic Acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-(4-Fluoro-phenyl)-4H,6H-1,2,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester was deprotected using trifluoroacetic acid and the resulting salt was coupled with (R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid using HOBT, EDC and DIPEA. The desired compound was obtained as a viscous oil.

Sources & evidence

ORD record
ord-6b7616d1ef024a4bab6caac8f2158360
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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