Triethylamine → HCID 71765631, compound

HRID 626851Notes

Reaction equation

HRID 626851 reaction equation
Cl.Cl.[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([CH:14]([C:16]3[CH:17]=[C:18]([Cl:30])[C:19]([C:28]#[N:29])=[C:20]4[C:26]=3[O:25][CH:24]([CH3:27])[CH2:23][NH:22][CH2:21]4)[CH3:15])[N:11]=[C:12]([CH3:13])[C:5]=12.C(N(CC)CC)C.Br.Br[CH2:40][C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1>CN(C)C=O>[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([CH:14]([C:16]3[CH:17]=[C:18]([Cl:30])[C:19]([C:28]#[N:29])=[C:20]4[C:26]=3[O:25][CH:24]([CH3:27])[CH2:23][N:22]([CH2:40][C:41]3[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=3)[CH2:21]4)[CH3:15])[N:11]=[C:12]([CH3:13])[C:5]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 86697543HCID 86697543, compound

Product 1

HCID 71765631HCID 71765631, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

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 bishydrochloride (0.020 g, 0.05 mmol) was taken up in N,N-dimethylformamide (2.0 mL) and triethylamine (0.034 mL, 0.24 mmol), and the 3-(bromomethyl)pyridine hydrobromide was added. The reaction was heated to 85° C. for 2 h and was allowed to cool. The product was purified by prep HPLC on C-18 column eluting water:acetonitrile gradient buffered pH 10 to give two diastereomers: Peak #1 (Example 59): LCMS calculated for C25H26ClN8O (M+H)+: m/z=489.2; found: 489.2; Peak #2 (Example 60): LCMS calculated for C25H26ClN8O (M+H)+: m/z=489.2; found: 489.2.

Workup

  1. temperatureto cool
  2. customThe product was purified by prep HPLC on C-18 column
  3. washeluting water
  4. customacetonitrile gradient buffered pH 10 to give two diastereomers

Sources & evidence

ORD record
ord-e274ea87cae848c1a1da7b11d943be1a
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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