Triethylamine → HCID 86677721, compound

HRID 1499796Notes

Reaction equation

HRID 1499796 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:14]([C:16]3[C:17]([O:34][CH3:35])=[C:18]([CH:25]4[CH2:28][N:27]([C@@H:29]([CH3:33])[C:30](O)=[O:31])[CH2:26]4)[C:19]([CH3:24])=[C:20]([C:22]#[N:23])[CH:21]=3)[CH3:15])[N:9]=[C:10]([CH:11]([F:13])[F:12])[C:3]=12.[Cl-].C[NH3+].[CH2:39]([N:41](CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O.C(#N)C>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:14]([C:16]3[C:17]([O:34][CH3:35])=[C:18]([CH:25]4[CH2:26][N:27]([C@@H:29]([CH3:33])[C:30]([NH:41][CH3:39])=[O:31])[CH2:28]4)[C:19]([CH3:24])=[C:20]([C:22]#[N:23])[CH:21]=3)[CH3:15])[N:9]=[C:10]([CH:11]([F:13])[F:12])[C:3]=12

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11637Methanamine, hydrochloride (1:1)HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86677722HCID 86677722, compound

Product 1

HCID 86677721HCID 86677721, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of (2S)-2-[3-(3-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-5-cyano-2-methoxy-6-methylphenyl)azetidin-1-yl]propanoic acid (30 mg, 0.06 mmol), methylammonium chloride (6.6 mg, 0.098 mmol) and triethylamine (18 μL, 0.13 mmol) in N,N-dimethylformamide (0.3 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (43 mg, 0.098 mmol). The resulting mixture was stirred for 3 h at room temperature. The mixture was diluted with acetonitrile, filtered, and purified using RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give 4.7 mg (10%, 3 steps) of the desired product. The product was isolated as mixture of diastereomers. LCMS calculated for C24H29F2N8O2 (M+H)+: m/z=499.2; Found: 499.1.

Workup

  1. filtrationfiltered
  2. custompurified
  3. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-9a5082b216e64f838a7bfbe70bb24ca3
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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