5,6-diamino-1-butyl-3-(2-fluorobenzyl)-1H-pyrimidine-2,4-dione → N-[6-amino-1-butyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-2-[5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-acetamide

HRID 858069Notes

Reaction equation

HRID 858069 reaction equation
C(NC1SC(S(NC2C=CC(CC([NH:24][C:25]3[C:26](=[O:45])[N:27]([CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=4[F:44])[C:28](=[O:36])[N:29]([CH2:32][CH:33]4[CH2:35][CH2:34]4)[C:30]=3[NH2:31])=O)=CC=2)(=O)=O)=C(C)N=1)(=O)C.[Cl:46][C:47]1[N:51]([CH3:52])[N:50]=[C:49]([CH3:53])[C:48]=1[S:54]([NH:57][C:58]1[CH:59]=[CH:60][C:61]([CH2:64][C:65]([OH:67])=O)=[N:62][CH:63]=1)(=[O:56])=[O:55].NC1C(=O)N(CC2C=CC=CC=2F)C(=O)N(CCCC)C=1N>>[NH2:31][C:30]1[N:29]([CH2:32][CH2:33][CH2:34][CH3:35])[C:28](=[O:36])[N:27]([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[F:44])[C:26](=[O:45])[C:25]=1[NH:24][C:65](=[O:67])[CH2:64][C:61]1[CH:60]=[CH:59][C:58]([NH:57][S:54]([C:48]2[C:49]([CH3:53])=[N:50][N:51]([CH3:52])[C:47]=2[Cl:46])(=[O:55])=[O:56])=[CH:63][N:62]=1

Participants

4

Reactant 3

HCID 218917565,6-diamino-1-butyl-3-(2-fluorobenzyl)-1H-pyrimidine-2,4-dioneHCID 58762844[5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-acetic acidHCID 587628482-[4-(2-acetylamino-4-methyl-thiazole-5-sulfonylamino)-phenyl]-N-[6-amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetamide

Product 1

HCID 58762841N-[6-amino-1-butyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-2-[5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-acetamide

Procedure

Prepared as for 2-[4-(2-acetylamino-4-methyl-thiazole-5-sulfonylamino)-phenyl]-N-[6-amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetamide (example 10, step 1) except using [5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-acetic acid and 5,6-diamino-1-butyl-3-(2-fluoro-benzyl)-1H-pyrimidine-2,4-dione. N-[6-amino-1-butyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-2-[5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-acetamide was used without purification (91%); LRMS for C27H30ClFN8O5S (M+H)+ at m/z=633/635.

Workup

  1. customN-[6-amino-1-butyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-2-[5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-acetamide was used without purification (91%)

Sources & evidence

ORD record
ord-edd8ff0c37d64356b7a05ac5fc314389
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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