1-Hydroxybenzotriazole → HCID 15435304, compound

HRID 617650Notes

Reaction equation

HRID 617650 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)[C:15]([C:23]2[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=CC=C[CH:3]=1.[NH2:30][CH:31]([CH3:44])[C:32](C1C=CC=CC=1)([OH:37])[C:33]([F:36])([F:35])[F:34].CCN=C=N[CH2:50][CH2:51][CH2:52]N(C)C.Cl.[CH:57]1[CH:58]=[CH:59][C:60]2N(O)N=N[C:61]=2[CH:62]=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:30][CH:31]([CH2:44][C:61]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:62]=2)[CH:32]([OH:37])[C:33]([F:36])([F:34])[F:35])=[O:22])[C:15]([C:23]2[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:3]=[CH:52][CH:51]=[CH:50][CH:7]=1.[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:30][CH:31]([CH2:44][C:61]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:62]=2)[C:32](=[O:37])[C:33]([F:36])([F:34])[F:35])=[O:22])[C:15]([C:23]2[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:3]=[CH:52][CH:51]=[CH:50][CH:7]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21851441HCID 21851441, compoundHCID 21851497HCID 21851497, compound

Product 2

HCID 15435304HCID 15435304, compoundHCID 21851489HCID 21851489, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[5-Benzyloxycarbonylamino-6-oxo-2-(m-tolyl)-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, 2-[5-benzyloxycarbonylamino-6-oxo-2-(m-tolyl)-1,6-dihydro-1-pyrimidinyl]acetic acid (title compound in Reference Example 5, 3.00 g, 7.63 mmol) was treated with 3-amino-1,1,1-trifluoro-2-phenyl-2-butanol (title compound in Reference Example 1, 1.76 g, 8.03 mmol), WSCI hydrochloride (1.76 g, 9.18 mmol) and HOBT (2.06 g, 15.2 mmol) in DMF (25 mL) to give 4.54 g (100%) of the target compound as colorless crystals.

Sources & evidence

ORD record
ord-d225218e86504dce9e3c56fe2f3d246f
Source dataset
uspto-grants-1999_09
Patent number
US05948785

Reaction notes

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