Hydroxylamine → HCID 86663941, compound

HRID 383253Notes

Reaction equation

HRID 383253 reaction equation
[NH2:1][OH:2].[NH:3]1[C:11]2[C:6](=[C:7]([C:12]3[N:13]=[C:14]([N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)[C:15]4[S:20][C:19]([CH2:21][N:22]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:23][CH2:24][CH2:25][C:26](OCC)=[O:27])=[CH:18][C:16]=4[N:17]=3)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4]1>>[C:34]([O:33][C:31](=[O:32])[N:22]([CH2:21][C:19]1[S:20][C:15]2[C:14]([N:38]3[CH2:39][CH2:40][O:41][CH2:42][CH2:43]3)=[N:13][C:12]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:6]=3[CH:5]=[N:4][NH:3]4)=[N:17][C:16]=2[CH:18]=1)[CH2:23][CH2:24][CH2:25][C:26]([NH:1][OH:2])=[O:27])([CH3:36])([CH3:35])[CH3:37]

Participants

3

Reactant 2

HCID 787HydroxylamineHCID 66977940HCID 66977940, compound

Product 1

HCID 86663941HCID 86663941, compoundYield 91%

Procedure

The freshly prepared hydroxylamine solution (6.00 mL) was placed in 50 mL flask. Compound 0405-41 (300 mg, 0.51 mmol) was added to this solution and degassed at room temperature for 30 minutes. The reaction process was monitored by TLC. The mixture was neutralized with dry ice, filtered, and the precipitation was washed with methanol and water to give tert-butyl(2-(1H-indazol-4-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl(4-(hydroxyamino)-4-oxobutyl)carbamate (267 mg, 91%) as a white solid. LCMS: 568 [M+1]+; 1H NMR (400 MHz, DMSO-d6):δ1.45 (s, 9H), 1.74 (m, 2H), 1.96 (t, J=7.2 Hz, 2H), 3.23 (m, 2H), 3.83 (m, 4H), 4.00 (m, 4H), 7.47 (t, J=8.0 Hz, 1H), 7.50 (s, 1H), 7.67 (d, J=8.0 Hz, 1H), 8.22 (d, J=8.0 Hz, 1H), 8.70 (s, 1H), 8.88 (s, 1H), 10.39 (s, 1H), 13.22 (s, 1H).

Workup

  1. customdegassed at room temperature for 30 minutes
  2. filtrationfiltered
  3. customthe precipitation
  4. washwas washed with methanol and water

Sources & evidence

ORD record
ord-7b9196b567d04b07a23e98aca529e844
Source dataset
uspto-grants-2013_02
Patent number
US08367663B2

Reaction notes

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