Triethylamine → HCID 58431372, compound

HRID 1617392Notes

Reaction equation

HRID 1617392 reaction equation
[F:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH:15]12[CH:23]([N:24]3[CH2:27][C:26]([CH2:50][C:51]#[N:52])([N:28]4[CH:32]=[C:31]([C:33]5[C:34]6[CH:41]=[CH:40][N:39](COCC[Si](C)(C)C)[C:35]=6[N:36]=[CH:37][N:38]=5)[CH:30]=[N:29]4)[CH2:25]3)[CH:19]([CH2:20][NH:21][CH2:22]1)[CH2:18][O:17][CH2:16]2.C(N(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=O)C>[F:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([N:21]1[CH2:20][CH:19]2[CH:23]([N:24]3[CH2:25][C:26]([CH2:50][C:51]#[N:52])([N:28]4[CH:32]=[C:31]([C:33]5[C:34]6[CH:41]=[CH:40][NH:39][C:35]=6[N:36]=[CH:37][N:38]=5)[CH:30]=[N:29]4)[CH2:27]3)[CH:15]([CH2:16][O:17][CH2:18]2)[CH2:22]1)=[O:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 265964893-Fluoro-2-(trifluoromethyl)isonicotinic acidHCID 67392488HCID 67392488, compound

Product 1

HCID 58431372HCID 58431372, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-fluoro-2-(trifluoromethyl)isonicotinic acid (50.0 mg, 0.239 mmol) and {1-(3-oxa-7-azabicyclo[3.3.1]non-9-yl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile (128 mg, 0.239 mmol) in DMF (2 mL) were added triethylamine (0.100 mL, 0.717 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (127 mg, 0.287 mmol). The mixture was stirred at room temperature for 2 hours. Direct purification with prep-LCMS (pH=10) afforded 50 mg (30% yield) of the desired product. LCMS found: 696.3 (M+1)+.

Workup

  1. customDirect purification with prep-LCMS (pH=10)

Sources & evidence

ORD record
ord-fc897c2282234118ac1faab1f7df599f
Source dataset
uspto-grants-2014_07
Patent number
US08765734B2

Reaction notes

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