1-Hydroxybenzotriazole → Ethyl 7-[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxylate

HRID 132880Notes

Reaction equation

HRID 132880 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[F:22])[CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[F:24][C:25]([F:42])([F:41])[C:26]1[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:34][C:33]2[CH2:32][CH2:31][NH:30][CH2:29][C:28]=2[N:27]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>C(Cl)CCl>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[F:22])[CH2:10][C:11]([N:30]1[CH2:29][C:28]2[N:27]=[C:26]([C:25]([F:42])([F:41])[F:24])[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:34][C:33]=2[CH2:32][CH2:31]1)=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11347588(R)-b-(Boc-amino)-2,5-difluorobenzenebutanoic acid2×HCID 69192352Ethyl 2-(Trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxylate hydrochloride2×

Product 1

HCID 69222346Ethyl 7-[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid (intermediate 1) and ethyl 2-(trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxylate hydrochloride (intermediate 27) were treated with EDC, HOBt and N,N-diisopropylethylamine according to the procedure described for Example 1, Step A to afford the title compound as a white foam.

Sources & evidence

ORD record
ord-904667328e8847629d13b0599d2a58cf
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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