Ammonium Hydroxide → HCID 58486287, compound

HRID 2383688Notes

Reaction equation

HRID 2383688 reaction equation
C([O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:25]4[C:20](=[CH:21][C:22]([C@H:26]5[C@@:28]6([C:36]7[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=7)[NH:30][C:29]6=[O:39])[CH2:27]5)=[CH:23][CH:24]=4)[NH:19][N:18]=3)=[CH:13][N:12]=2)[CH2:7][CH2:6]1)(=O)C.[NH4+].[OH-]>CO>[OH:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[CH:13][C:14]([C:17]3[C:25]4[C:20](=[CH:21][C:22]([C@H:26]5[C@@:28]6([C:36]7[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=7)[NH:30][C:29]6=[O:39])[CH2:27]5)=[CH:23][CH:24]=4)[NH:19][N:18]=3)=[CH:15][CH:16]=2)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 67449090HCID 67449090, compound

Product 1

HCID 58486287HCID 58486287, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(5-(6-((1R*,2S*)-5′-methoxy-2′-oxospiro[cyclopropane-1,3′-indoline]-2-yl)-1H-indazol-3-yl)pyridin-2-yl)piperidin-4-yl acetate (40 mg, 0.076 mmol) and aqueous NH4OH (0.03 mL, 14 M) in MeOH (3 mL) was stirred at rt for 17 h. The crude reaction mixture was concentrated under reduced pressure to dryness, and the resulting crude product was purified by preparative HPLC to give the title compound as a yellow solid and as the TFA salt (23 mg, 62%). 1H NMR (400 MHz, MeOD) δ 8.56 (dd, J=9.6, 2.0 Hz, 1H), 8.37 (d, J=1.6 Hz, 1H), 7.86 (d, J=8.5 Hz, 1H), 7.54 (s, 1H), 7.49 (d, J=9.6 Hz, 1H), 7.05 (d, J=8.5 Hz, 1H), 6.83 (d, J=8.4 Hz, 1H), 6.60 (dd, J=8.4, 2.4 Hz, 1H), 5.60 (d, J=2.3 Hz, 1H), 4.06-3.99 (m, 3H), 3.65-3.59 (m, 2H), 3.37-3.35 (m, 1H), 3.28 (s, 3H), 2.26-2.23 (m, 1H), 2.20-2.16 (m, 2H), 2.09-2.04 (m, 2H), 1.78-1.69 (m, 2H); MS ESI 482.3 [M+H]+, calcd for [C28H27N5O3+H]+ 482.21.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under reduced pressure to dryness
  3. customthe resulting crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-39a6c55a5fb24913aaf1be3226ce746f
Source dataset
uspto-grants-2012_09
Patent number
US08263596B2

Reaction notes

Loading…