Sodium Hydroxide → HCID 118130630, compound

HRID 1486960Notes

Reaction equation

HRID 1486960 reaction equation
[Cl:1][C:2]1[CH:43]=[CH:42][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:19]3[C:36]4[C:31](=[C:32]([C:38](F)(F)F)[CH:33]=[CH:34][C:35]=4[OH:37])[C:21]4([CH2:26][CH2:25][N:24]([CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:23][CH2:22]4)[CH2:20]3)=[O:11])[S:8][C:4]=2[CH:3]=1.[OH-].[Na+].[OH-].[NH4+:47]>>[Cl:1][C:2]1[CH:43]=[CH:42][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:19]3[C:36]4[C:31](=[C:32]([C:38]#[N:47])[CH:33]=[CH:34][C:35]=4[OH:37])[C:21]4([CH2:26][CH2:25][N:24]([CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:23][CH2:22]4)[CH2:20]3)=[O:11])[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 118130628HCID 118130628, compound

Product 1

HCID 118130630HCID 118130630, compound

Conditions

Temperature
40 °C

Procedure

To 1-(6-chlorobenzo[d]thiazol-2-yl)-3-(2-(7-hydroxy-1′-isobutyl-4-(trifluoromethyl)spiro[indoline-3,4′-piperidine]-1-yl)phenyl)urea (Example 30, 6.0 mg, 9.5 μmol) was added sodium hydroxide (95 μL, 0.095 mmol) and ammonium hydroxide (27.5 μL, 0.190 mmol). The reaction mixture was stirred at 40° C. for 18 h. The crude product was purified using a 10 minutes gradient from 0 to 100% B and pump to dryness to give the title compound Example 80 (3.5 mg, 6.0 μmol, 63% yield). 1H NMR (400 MHz, MeOD) δ ppm 1.01 (d, J=6.60 Hz, 6H), 2.12 (t, J=14.02 Hz, 3H), 2.54-2.67 (m, 1H), 2.86 (m, 1H), 2.92 (d, J=7.15 Hz, 2H), 3.01 (t, J=12.09 Hz, 1H), 3.08-3.17 (m, 1H), 3.56 (d, J=10.44 Hz, 3H), 4.20 (d, J=10.44 Hz, 1H), 6.75 (d, J=8.24 Hz, 1H), 7.03-7.14 (m, 3H), 7.16-7.26 (m, 2H), 7.30 (m, 1H), 7.59 (dd, J=8.52, 2.47 Hz, 1H), 8.10 (d, J=7.15 Hz, 1H). LCMS (ESI) m/z 587.4 (M+H)+, RT=1.69 min (Method D).

Workup

  1. customThe crude product was purified
  2. waitusing a 10 minutes gradient from 0 to 100% B and pump to dryness

Sources & evidence

ORD record
ord-a4d08c20e46e4b5888480283fa4d32e0
Source dataset
uspto-grants-2016_08
Patent number
US09428504B2

Reaction notes

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