(S)-(+)-1-Aminopropan-2-ol → HCID 57856352, compound

HRID 500742Notes

Reaction equation

HRID 500742 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[C:23]([C:24]5[CH:29]=[CH:28][N:27]=[C:26](S(C)(=O)=O)[N:25]=5)=[CH:22][N:21]([CH2:34][C:35]#[N:36])[N:20]=4)[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:37][CH2:38][C@@H:39]([OH:41])[CH3:40]>C1COCC1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[C:23]([C:24]5[CH:29]=[CH:28][N:27]=[C:26]([NH:37][CH2:38][C@@H:39]([OH:41])[CH3:40])[N:25]=5)=[CH:22][N:21]([CH2:34][C:35]#[N:36])[N:20]=4)[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 57856283HCID 57856283, compound

Product 1

HCID 57856352HCID 57856352, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A Mixture of the [3-(1-Benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-4-(2-methanesulfonyl-pyrimidin-4-yl)-pyrazol-1-yl]-acetonitrile (C-1-5) (310 mg, 0.6 mmol) and (S)-(+)-1-amino-2-propanol (134 mg, 1.8 mmol) in THF (5 mL) was heated at 80° C. for 18 hr. The mixture was concentrated onto silica gel then purified on silica gel using a gradient of 0-6% methanol in a mixture of dichloromethane and ethyl acetate (1:1) as eluent to yield 220 mg (72%) of {3-(1-Benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-4-[2-((S)-2-hydroxy-propylamino)-pyrimidin-4-yl]-pyrazol-1-yl}-acetonitrile (C-1-6) as a foam from methyl tert-butyl ether. 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm 8.52 (d, J=2.02 Hz, 1H), 8.20 (s, 1H), 8.07-8.17 (m, 4H), 7.81 (d, J=4.04 Hz, 1H), 7.63-7.73 (m, 1H), 7.52-7.60 (m, 2H), 6.75 (d, J=4.04 Hz, 1H), 6.53 (br. s., 1H), 5.67 (br. t, J=4.93 Hz, 1H), 5.24 (s, 2H), 3.56 (br. s., 1H), 2.64-3.28 (br. m, 3H), 0.74 (br. s., 3H).

Workup

  1. concentrationThe mixture was concentrated onto silica gel
  2. customthen purified on silica gel using a gradient of 0-6% methanol
  3. additionin a mixture of dichloromethane and ethyl acetate (1:1) as eluent

Sources & evidence

ORD record
ord-e6c4d748a7fc4ddf97547f321cddc817
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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