Water → HCID 58169183, compound

HRID 1484975Notes

Reaction equation

HRID 1484975 reaction equation
C([O:4][CH2:5][CH2:6][CH:7]([C:9]1[S:10][C:11]([C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[C:24]([CH:26]4[CH2:28][CH2:27]4)[NH:23][N:22]=3)[C:17]([C:29]#[CH:30])=[CH:16][N:15]=2)=[CH:12][CH:13]=1)[OH:8])(=O)C.O>CO>[CH:26]1([C:24]2[NH:23][N:22]=[C:21]([NH:20][C:18]3[C:17]([C:29]#[CH:30])=[CH:16][N:15]=[C:14]([C:11]4[S:10][C:9]([CH:7]([OH:8])[CH2:6][CH2:5][OH:4])=[CH:13][CH:12]=4)[N:19]=3)[CH:25]=2)[CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 962WaterHCID 58169459HCID 58169459, compound

Product 1

HCID 58169183HCID 58169183, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-yl)-3-hydroxypropyl acetate C-243 (390 mg, 0.92 mmol, 1.0 equiv.) in MeOH (10 mL) was stirred at 23° C., 1 NNaOH was added until the PH of the solution reached 11˜12. After 1 hour, H2O (20 mL) and 1 NHCl were added until the PH of the solution reached 3-4. The reaction mixture was extracted with THF and washed with water, brine, dried and evaporated. The crude product was crystallized with THF/isopropyl to afford 1-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-yl)propane-1,3-diol (Compound 242) (250 mg, 71.3%). LC-MS (m/z)=382.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.75 (m, 2H), 0.98-1.00 (m, 2H), 1.84-1.88 (m, 2H), 1.93-1.98 (m, 1H), 3.47-3.59 (m, 2H), 4.53 (t, J=4.8 Hz, 1H), 4.84 (s, 1H), 4.92-4.96 (m, 1H), 5.72 (d, J=4.8 Hz, 1H), 6.54 (s, 1H), 7.02 (d, J=3.6 Hz, 1H), 7.72 (d, J=3.2 Hz, 1H), 8.45 (s, 1H), 8.55 (s, 1H), 12.27 (s, 1H).

Workup

  1. extractionThe reaction mixture was extracted with THF
  2. washwashed with water, brine
  3. customdried
  4. customevaporated
  5. customThe crude product was crystallized with THF/isopropyl

Sources & evidence

ORD record
ord-95daad091afa4985a63b60ae50353184
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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