Sodium Bicarbonate → 2-(benzo[d]oxazol-2-yl)-N-(4-(3-(4-(dimethylamino)piperidin-1-yl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)acetamide

HRID 2241336Notes

Reaction equation

HRID 2241336 reaction equation
[NH2:1][C:2]1[CH:35]=[CH:34][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[N:13](CC4C=CC(OC)=CC=4)[N:14]=[C:15]([N:16]4[CH2:21][CH2:20][CH:19]([N:22]([CH3:24])[CH3:23])[CH2:18][CH2:17]4)[C:8]=23)=[C:4]([F:36])[CH:3]=1.[O:37]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[N:39]=[C:38]1[CH2:46][C:47](O)=[O:48].C([O-])(O)=O.[Na+]>>[O:37]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[N:39]=[C:38]1[CH2:46][C:47]([NH:1][C:2]1[CH:35]=[CH:34][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[NH:13][N:14]=[C:15]([N:16]4[CH2:21][CH2:20][CH:19]([N:22]([CH3:24])[CH3:23])[CH2:18][CH2:17]4)[C:8]=23)=[C:4]([F:36])[CH:3]=1)=[O:48]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 954457(1,3-Benzoxazol-2-yl)acetic acidHCID 685138871-(1-(4-methoxybenzyl)-4-(4-amino-2-fluorophenoxy)-1H-pyrazolo[3,4-b]pyridin-3-yl)-N,N-dimethylpiperidin-4-amine

Product 1

HCID 593041812-(benzo[d]oxazol-2-yl)-N-(4-(3-(4-(dimethylamino)piperidin-1-yl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)acetamideYield 80%

Procedure

Prepared by a 2-step process from 1-(4-(4-amino-2-fluorophenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)-N,N-dimethylpiperidin-4-amine (prepared as in Example 93, Step A) and 2-(benzo[d]oxazol-2-yl)acetic acid according to the procedure of Example 21, Steps A and B, except that the crude was treated with aqueous NaHCO3 solution to remove TFA. The crude was rinsed with Et2O to afford 13 mg (80%) of the desired product. LRMS (ESI pos) m/e 530.1 (M+1). 1H-NMR (400 MHz, CD3OD/CDCl3) δ 8.20 (d, 1H), 7.86 (dd, 1H), 7.72 (m, 1H), 7.60 (m, 1H), 7.41 (m, 3H), 7.30 (t, 1H), 6.22 (d, 1H), 4.15 (m, 2H), 2.95 (t, 3H), 2.64 (s, 6H), 2.09 (m, 2H), 1.84 (m, 2H); 19F-NMR (376 MHz, CD3OD/CDCl3) δ −128.7.

Workup

  1. customto remove TFA
  2. washThe crude was rinsed with Et2O

Sources & evidence

ORD record
ord-3f576141ab5d41878cb43e71b0acc99f
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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