1-Hydroxybenzotriazole → HCID 21851338, compound

HRID 617662Notes

Reaction equation

HRID 617662 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20](O)=[O:21])[C:15]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:28][CH:29]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH:30]([OH:35])[C:31]([F:34])([F:33])[F:32].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:28][CH:29]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:30]([OH:35])[C:31]([F:32])([F:33])[F:34])=[O:21])[C:15]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][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:28][CH:29]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:30](=[O:35])[C:31]([F:33])([F:34])[F:32])=[O:21])[C:15]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10022973HCID 10022973, compoundHCID 145032493-Amino-1,1,1-trifluoro-4-phenylbutan-2-ol

Product 2

HCID 21851338HCID 21851338, compoundHCID 21851449HCID 21851449, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[5-Benzyloxycarbonylamino-6-oxo-2-(2-thienyl)-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-6-oxo-2-(2-thienyl)-1,6-dihydro-1-pyrimidinyl]acetic acid (title compound in Reference Example 19, 2.00 g, 4.84 mmol) was treated with 3-amino-1,1,1-trifluoro-4-phenyl-2-butanol (title compound in Reference Example 1, 1.11 g, 5.06 mmol), WSCI hydrochloride (1.11 g, 5.79 mmol) and HOBT (1.31 g, 9.69 mmol) in DMF (20 mL) to give 2.66 g (94%) of the target compound as pale-yellow crystals.

Sources & evidence

ORD record
ord-71205f9eae7843bc9acad9c9a9e30de0
Source dataset
uspto-grants-1999_09
Patent number
US05948785

Reaction notes

Loading…