4-Amino-3-fluorobenzamide → 3-Fluoro-4-({4-[({2-[methyl(methylsulfonyl)amino]pyridin-3-yl}methyl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)benzamide formic acid salt

HRID 2077073Notes

Reaction equation

HRID 2077073 reaction equation
[CH:1]([OH:3])=[O:2].F[C:5]1[CH:13]=[C:12]([NH:14][C:15]2[N:20]=[C:19]([NH:21][CH2:22][C:23]3[C:24]([N:29]([CH3:34])[S:30]([CH3:33])(=[O:32])=[O:31])=[N:25][CH:26]=[CH:27][CH:28]=3)[C:18]([C:35]([F:38])([F:37])[F:36])=[CH:17][N:16]=2)[CH:11]=[CH:10][C:6]=1[C:7]([NH2:9])=[O:8].NC1C=CC(C(N)=O)=CC=1[F:49]>C(O)=O>[CH:1]([OH:3])=[O:2].[F:49][C:13]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:14][C:15]1[N:20]=[C:19]([NH:21][CH2:22][C:23]2[C:24]([N:29]([CH3:34])[S:30]([CH3:33])(=[O:32])=[O:31])=[N:25][CH:26]=[CH:27][CH:28]=2)[C:18]([C:35]([F:36])([F:38])[F:37])=[CH:17][N:16]=1)[C:7]([NH2:9])=[O:8]

Participants

4

Reactant 2

HCID 121180534-Amino-3-fluorobenzamideHCID 251171272-Fluoro-4-({-4-[({2-[methyl(methylsulfonyl)amino]pyridin-3-yl}methyl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)benzamide formic acid salt

Product 1

HCID 251173463-Fluoro-4-({4-[({2-[methyl(methylsulfonyl)amino]pyridin-3-yl}methyl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)benzamide formic acid salt

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Compound 14 was prepared in a manner similar to that described Example 13 for the preparation of 13 except that 4-amino-3-fluorobenzamide (1.5 equ/189 μM) was used instead of 4-amino-2-fluorobenzamide to provide the formic acid salt of 14 as a cream colored solid. Yield: 26 mg, 37%. LC-MS M+1=514. NMR (d6-DMSO) : 2.98 (3H, s), 3.09 (3H, s), 4.65 (2H, s), 7.35-7.66 (7H, m), 7.87 (1H, s), 8.23 (1H, s), 8.38 (1H, s), 9.19 (1H, s). FAK IC50: <0.000595 μM (Table 1, Example 322)

Workup

  1. customCompound 14 was prepared in a manner similar to

Sources & evidence

ORD record
ord-af0ed3cfe5cd45b0b2028126a990e653
Source dataset
uspto-grants-2011_04
Patent number
US07928109B2

Reaction notes

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