Triethylamine → HCID 71765593, compound

HRID 626848Notes

Reaction equation

HRID 626848 reaction equation
Br[CH2:2][C:3]([NH2:5])=[O:4].Cl.Cl.Cl.[NH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]2[N:16]([CH:20]([C:22]3[CH:23]=[C:24]([Cl:40])[C:25]([C:38]#[N:39])=[C:26]4[C:32]=3[O:31][CH:30]([CH3:33])[CH2:29][N:28]([CH:34]3[CH2:37][NH:36][CH2:35]3)[CH2:27]4)[CH3:21])[N:17]=[C:18]([CH3:19])[C:11]=12.C(N(CC)CC)C>CN(C)C=O>[NH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]2[N:16]([CH:20]([C:22]3[C:32]4[O:31][CH:30]([CH3:33])[CH2:29][N:28]([CH:34]5[CH2:37][N:36]([CH2:2][C:3]([NH2:5])=[O:4])[CH2:35]5)[CH2:27][C:26]=4[C:25]([C:38]#[N:39])=[C:24]([Cl:40])[CH:23]=3)[CH3:21])[N:17]=[C:18]([CH3:19])[C:11]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 696322-BromoacetamideHCID 86697541HCID 86697541, compound

Product 1

HCID 71765593HCID 71765593, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromoacetamide (0.01 g, 0.09 mmol) was added to a mixture of 9-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-4-azetidin-3-yl-7-chloro-2-methyl-2,3,4,5-tetrahydro-1,4-benzoxazepine-6-carbonitrile trishydrochloride (20 mg, 0.04 mmol) and triethylamine (20 μL, 0.18 mmol) in N,N-dimethylformamide (2 mL) and then heated to 80° C. for 2 h. The reaction was allowed to cool and was purified without work up by prep HPLC on a C-18 column eluting water:acetonitrile gradient buffered pH 10 to give the title compounds as two separated diastereomers: Peak #1 (Example 50): LCMS calculated for C24H29ClN9O2 (M+H)+: m/z=510.2; found: 510.2; Peak #2 (Example 51): LCMS calculated for C24H29ClN9O2 (M+H)+: m/z=510.2; found: 510.2.

Workup

  1. temperatureto cool
  2. customwas purified without work up by prep HPLC on a C-18 column
  3. washeluting water

Sources & evidence

ORD record
ord-c7244ca0bcc048eab8e673ac2fd39396
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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