Methanol → HCID 178514149, compound

HRID 45008Notes

Reaction equation

HRID 45008 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][S:28][C:29]#[N:30])[CH2:23][CH2:22]4)[CH:20]=3)[C:10]=2[CH:9]=[CH:8]1.CO.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[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][S:28][C:29]#[N:30])[CH2:25][CH2:26]3)[CH:20]=2)=[N:14][CH:13]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 178504223HCID 178504223, compound

Product 1

HCID 178514149HCID 178514149, 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]cyclohexylmethyl thiocyanate was dissolved in methanol (2.0 mL, 0.049 mol) and DCM (2.0 mL, 0.031 mol), and TFA (0.5 mL, 0.006 mol) was added. The resulting mixture was stirred at 25° C. for 16 hours. TLC analysis showed no starting material present and LCMS analysis showed product. The reaction was concentrated using a rotary evaporator and the concentrate was chromatographed on silica gel using 2% MeOH/EtOAc to give the product. LC/MS (M+H)+: 339, 1H NMR(CD3OD) δ 8.65 (s, 1H), 8.55 (s, 1H), 8.31 (s, 1H), 7.50 (d, 1H), 6.96 (d, 1H), 4.43 (m, 1H), 3.20 (d, 2H, J=7.6 Hz), 2.24 (m, 2H), 1.80-2.17 (m, 7H).

Workup

  1. concentrationThe reaction was concentrated
  2. customa rotary evaporator
  3. customthe concentrate was chromatographed on silica gel using 2% MeOH/EtOAc
  4. customto give the product

Sources & evidence

ORD record
ord-18fd4e875d10484da0b8de590db9cad3
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Reaction notes

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