2-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride salt → 2-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-N-benzylnicotinamide, dihydrochloride salt

HRID 1986073Notes

Reaction equation

HRID 1986073 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[C:12]([NH:17][C:18]2[CH:33]=[CH:32][C:21]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25](C(N)=O)[CH:24]=3)=[C:20]([F:34])[CH:19]=2)=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:35].[NH2:36]C1C=C(OC2C=CC(NC3N=CC=CC=3C(NC3C=CC(F)=CC=3F)=O)=CC=2F)C=CN=1>>[ClH:35].[ClH:35].[NH2:36][C:25]1[CH:24]=[C:23]([O:22][C:21]2[CH:32]=[CH:33][C:18]([NH:17][C:12]3[N:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:9]([NH:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])=[CH:19][C:20]=2[F:34])[CH:28]=[CH:27][N:26]=1

Participants

3

Reactant 2

HCID 162231052-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride saltHCID 577213414-(4-(3-(Benzylcarbamoyl)pyridin-2-ylamino)-2-fluorophenoxy)picolinamide

Product 1

HCID 1317274812-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenylamino)-N-benzylnicotinamide, dihydrochloride saltYield 69%

Procedure

4-(4-(3-(Benzylcarbamoyl)pyridin-2-ylamino)-2-fluorophenoxy)picolinamide (0.068 g, 0.15 mmol) was converted to the title compound (0.051 g, 69%) in a manner similar to the preparation of 2-(4-(2-aminopyridin-4-yloxy)-3-fluorophenylamino)-N-(2,4-difluorophenyl)nicotinamide (Step E of Example 3). 1H NMR (DMSO-d6) δ 11.17 (s, 1H), 9.44 (t, 1H, J=5.7 Hz), 8.10-8.35 (m, 3H), 7.91 (d, 1H, J=7.2 Hz), 7.82 (br s, 2H), 7.15-7.42 (m, 7H), 6.90-6.94 (m, 1H), 6.65 (dd, 1H, J=7.2, 2.5 Hz), 6.12 (d, 1H, J=2.5 Hz), 4.45 (d, 2H, J=5.8 Hz); HRMS(ESI+), 430.1679 (M+H)+ calc, 430.1683 (M+H)+ found.

Sources & evidence

ORD record
ord-9834e026611d491382c5d2fe5f542be5
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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