1-Hydroxybenzotriazole → HCID 21851332, compound

HRID 617659Notes

Reaction equation

HRID 617659 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([OH:22])=[O:21])[C:15]([C:23]2[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[C:25]([N+:32]([O-:34])=[O:33])[CH:24]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:35][CH:36]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH:37]([OH:42])[C:38]([F:41])([F:40])[F:39].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:35][CH:36]([CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:37]([OH:42])[C:38]([F:39])([F:40])[F:41])=[O:22])[C:15]([C:23]2[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[C:25]([N+:32]([O-:34])=[O:33])[CH:24]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:35][CH:36]([CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:37](=[O:42])[C:38]([F:39])([F:40])[F:41])=[O:21])[C:15]([C:23]2[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[C:25]([N+:32]([O-:34])=[O:33])[CH:24]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 145032493-Amino-1,1,1-trifluoro-4-phenylbutan-2-olHCID 21851386HCID 21851386, compound

Product 2

HCID 21851332HCID 21851332, compoundHCID 21851382HCID 21851382, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[5-Benzyloxycarbonylamino-2-(3,5-dinitrophenyl)-6-oxo-1,6-dihydro-1-pyrimidyl]-N-(1-benzyl-3,3,3-trifluoro-2-hydroxypropyl)-acetamide was synthesized in the same manner as in Example 1. That is, [5-benzyloxycarbonylamino-2-(3,5-dinitrophenyl)-6-oxo-1,6-dihydro-1-pyrimidinyl]acetic acid (title compound in Reference Example 16, mixture with diethyl ether, 3.74 g, 7.08 mmol) was treated with 3-amino-1,1,1-trifluoro-4-phenyl-2-butanol (title compound in Reference Example 1, 1.78 g, 8.12 mmol), WSCI hydrochloride (1.63 g, 8.50 mmol) and HOBT (1.91 g, 14.1 mmol) in DMF (25 mL) to give 4.06 g (86%) of the target compound as a dark-brown solid.

Sources & evidence

ORD record
ord-88c176277cb2429088551e6c5a113bc3
Source dataset
uspto-grants-1999_09
Patent number
US05948785

Reaction notes

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