Acetaldehyde → HCID 67446671, compound

HRID 447546Notes

Reaction equation

HRID 447546 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[C@:13]12[CH2:21][C@H:20]1[C:22]1[CH:30]=[C:29]2[C:25]([C:26]([C:31]3[CH:36]=[CH:35][C:34]([N:37]4[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]4)=[CH:33][CH:32]=3)=[N:27][NH:28]2)=[CH:24][CH:23]=1.[CH:43](=O)[CH3:44]>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:43]([N:40]1[CH2:41][CH2:42][N:37]([C:34]2[CH:33]=[CH:32][C:31]([C:26]3[C:25]4[C:29](=[CH:30][C:22]([C@H:20]5[C@@:13]6([C:12]7[C:16](=[CH:17][CH:18]=[C:10]([O:9][CH3:8])[CH:11]=7)[NH:15][C:14]6=[O:19])[CH2:21]5)=[CH:23][CH:24]=4)[NH:28][N:27]=3)=[CH:36][CH:35]=2)[CH2:38][CH2:39]1)[CH3:44]

Participants

3

Reactant 2

HCID 177AcetaldehydeHCID 67448475HCID 67448475, compound

Product 1

HCID 67446671HCID 67446671, compoundYield 7.2%

Procedure

The title compound was synthesized according to the method of Example A96B, using (1R*,2S*)-5′-methoxy-2-(3-(4-(piperazin-1-yl)phenyl)-1H-indazol-6-yl)spiro [cyclopropane-1,3′-indolin]-2′-one 2,2,2-trifluoroacetate (40 mg, 0.069 mmol) and acetaldehyde (6.0 uL, 0.140 mmol). The crude reaction mixture was concentrated under reduced pressure to dryness, and purified by preparative HPLC to give the title compound as a white solid (3.0 mg, 7.0%); 1H NMR (400 MHz, CD3OD) δ 7.91 (d, J=8.6 Hz, 1H), 7.87 (d, J=8.5 Hz, 2H), 7.49 (s, 1H), 7.17 (d, J=8.6 Hz, 2H), 7.02 (d, J=8.8 Hz, 1H), 6.82 (d, J=8.5 Hz, 1H), 6.60 (d, J=8.9 Hz, 1H), 5.60 (s, 1H), 4.02-4.92 (m, 2H), 3.74-3.64 (m, 2H), 3.38-3.22 (m, 5H), 3.28 (s, 3H), 3.14-3.05 (m, 2H), 2.26-2.22 (m, 1H), 2.20-2.16 (m, 1H), 1.41 (t, J=7.2 Hz, 3H); MS ESI [M+H]+ 494.3, calcd for [C30H31N5O2+H]+ 494.26.

Workup

  1. customThe title compound was synthesized
  2. customThe crude reaction mixture
  3. concentrationwas concentrated under reduced pressure to dryness
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-8b75566366d5451d876f11a8debeb227
Source dataset
uspto-grants-2013_07
Patent number
US08481525B2

Reaction notes

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