Ammonium Hydroxide → HCID 58486287, compound

HRID 1466369Notes

Reaction equation

HRID 1466369 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-c0a975fd9c66451da6680fc122163c69
Source dataset
uspto-grants-2015_04
Patent number
US08999968B2

Reaction notes

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