Acetic Anhydride → HCID 71765099, compound

HRID 626855Notes

Reaction equation

HRID 626855 reaction equation
Cl.Cl.Cl.[NH2:4][CH:5]1[CH2:8][CH:7]([N:9]2[CH2:15][C:14]3=[C:16]([C:34]#[N:35])[C:17]([Cl:33])=[CH:18][C:19]([CH:20]([N:22]4[C:26]5=[N:27][CH:28]=[N:29][C:30]([NH2:31])=[C:25]5[C:24]([CH3:32])=[N:23]4)[CH3:21])=[C:13]3[O:12][CH:11]([CH3:36])[CH2:10]2)[CH2:6]1.C(N(CC)CC)C.[C:44](OC(=O)C)(=[O:46])[CH3:45]>CN(C)C=O>[NH2:31][C:30]1[N:29]=[CH:28][N:27]=[C:26]2[N:22]([CH:20]([C:19]3[C:13]4[O:12][CH:11]([CH3:36])[CH2:10][N:9]([CH:7]5[CH2:6][CH:5]([NH:4][C:44](=[O:46])[CH3:45])[CH2:8]5)[CH2:15][C:14]=4[C:16]([C:34]#[N:35])=[C:17]([Cl:33])[CH:18]=3)[CH3:21])[N:23]=[C:24]([CH3:32])[C:25]=12

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 86697546HCID 86697546, compound

Product 1

HCID 71765099HCID 71765099, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The crude 4-(3-aminocyclobutyl)-9-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-7-chloro-2-methyl-2,3,4,5-tetrahydro-1,4-benzoxazepine-6-carbonitrile trishydrochloride was dissolved in N,N-dimethylformamide (2 mL) and triethylamine (10 μL, 0.1 mmol). To this mixture was added acetic anhydride (7.7 mg, 0.075 mmol). The reaction was stirred for 1 h at room temperature, and the reaction was purified without workup by prep HPLC on C-18 column eluting water:acetonitrile gradient buffered pH 10 to give two diastereomers: Peak #1 (Example 67): LCMS calculated for C25H30ClN8O2 (M+H)+: m/z=509.2; found: 509.2; Peak #2 (Example 68): LCMS calculated for C25H30ClN8O2 (M+H)+: m/z=509.2; found: 509.2.

Workup

  1. customthe reaction was purified without workup by prep HPLC on C-18 column
  2. washeluting water
  3. customacetonitrile gradient buffered pH 10 to give two diastereomers

Sources & evidence

ORD record
ord-cdc194138cfc4a87b67609beb4ce3441
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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