Methanol → HCID 178511081, compound

HRID 45006Notes

Reaction equation

HRID 45006 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15]([C:16]3[CH:17]=[N:18][N:19]([C@@H:21]4[CH2:26][CH2:25][C@H:24]([CH2:27][C:28]#[N:29])[CH2:23][CH2:22]4)[CH:20]=3)[C:10]=2[CH:9]=[CH:8]1.C(O)(C(F)(F)F)=O.C(Cl)Cl.CO.[OH-].[NH4+]>>[N:12]1[C:11]2[NH:7][CH:8]=[CH:9][C:10]=2[C:15]([C:16]2[CH:17]=[N:18][N:19]([C@@H:21]3[CH2:22][CH2:23][C@H:24]([CH2:27][C:28]#[N:29])[CH2:25][CH2:26]3)[CH:20]=2)=[N:14][CH:13]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 178504218HCID 178504218, compound

Product 1

HCID 178511081HCID 178511081, compound

Conditions

Temperature
25 °C

Procedure

cis-4-[4-(7-[2-(Trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclohexylacetonitrile (0.080 g, 0.00018 mol) and TFA (0.50 mL, 0.0065 mol) were added to DCM (3.00 mL, 0.0468 mol) and the mixture was stirred at 25° C. for 16 hours. The reaction was concentrated by roto-evaporation and the concentrate was dissolved in methanol (3.0 mL, 0.074 mol) and ammonium hydroxide (0.5 mL, 0.01 mol) was added This reaction was stirred at 25° C. for 6 hours at which time LCMS analysis showed no starting material present. The reaction was chromatographed on silica gel using 5% MeOH/EtOAc to give the product. LC/MS (M+H)+: 307, 1H NMR(CD3OD): δ 8.64 (s, 1H), 8.55 (s, 1H), 8.31 (s, 1H), 7.50 (d, 1H), 6.96 (d, 1H), 4.42 (m, 1H), 2.61 (d, 2H, J=8.0 Hz), 2.27 (m, 2H), 1.70-2.15 (m, 7H).

Workup

  1. concentrationThe reaction was concentrated by roto-evaporation
  2. stirringwas stirred at 25° C. for 6 hours at which time LCMS analysis
  3. customThe reaction was chromatographed on silica gel using 5% MeOH/EtOAc
  4. customto give the product

Sources & evidence

ORD record
ord-c9c76f72021d446eaadfe11e73f283c2
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Reaction notes

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