Isopropylamine → HCID 67959746, compound

HRID 1529453Notes

Reaction equation

HRID 1529453 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[CH:11]=[C:12]4[C:16](=[CH:17][CH:18]=3)[NH:15][CH:14]=[C:13]4[C:19]3[CH:24]=[C:23]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)[N:22]=[C:21](S(C)(=O)=O)[N:20]=3)[CH:7]=[N:6][CH:5]=2)[CH2:3][CH2:2]1.[CH:39]([NH2:42])([CH3:41])[CH3:40]>CN1C(=O)CCC1.O>[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[CH:11]=[C:12]4[C:16](=[CH:17][CH:18]=3)[NH:15][CH:14]=[C:13]4[C:19]3[CH:24]=[C:23]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)[N:22]=[C:21]([NH:42][CH:39]([CH3:41])[CH3:40])[N:20]=3)[CH:7]=[N:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 6363IsopropylamineHCID 67959779HCID 67959779, compound

Product 1

HCID 67959746HCID 67959746, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A glass microwave reaction vessel was charged with 5-(6-cyclopropylpyrazin-2-yl)-3-(6-(4-methoxybenzyloxy)-2-(methylsulfonyl)pyrimidin-4-yl)-1H-indole (26 mg, 0.049 mmol) and isopropylamine (0.4 ml, 4.66 mmol) in NMP (0.5 mL). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 120° C. for 1 h. The mixture was diluted with water and extracted with CHCl3/iPrOH (4:1). The combined organic layer was washed with water, dried, filtered and concentrated to give the crude compound, which was used in the next step without further purification. MS (ESI, pos. ion) m/z: 507.0 (M+1).

Workup

  1. customA glass microwave reaction vessel
  2. extractionextracted with CHCl3/iPrOH (4:1)
  3. washThe combined organic layer was washed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c3d6a0efbf3147c2ae96deb30fb27acc
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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