Water → HCID 86717402, compound

HRID 57644Notes

Reaction equation

HRID 57644 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]([NH:18][CH2:19][C@H:20]3[O:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]3)[C:15]3[C:10](=[N:11][CH:12]=[CH:13][N:14]=3)[CH:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:40][CH2:41][CH2:42][OH:43].O>CN(C=O)C>[OH:43][CH2:42][CH2:41][CH2:40][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:17]=[C:16]([NH:18][CH2:19][C@H:20]3[O:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]3)[C:15]3[C:10](=[N:11][CH:12]=[CH:13][N:14]=3)[CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 123083-Bromo-1-propanolHCID 136408075HCID 136408075, compound

Product 1

HCID 86717402HCID 86717402, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (R)-tert-butyl 2-((7-(4-hydroxyphenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate (115 mg, 0.26 mmol) in DMF (5 mL) was added Cs2CO3 (128 mg, 0.39 mmol) and 3-bromopropan-1-ol (55 mg, 0.39 mmol). The reaction was stirred at 80° C. for 0.5 hours. TLC and LC-Ms showed the reaction had completed and the reaction was poured into water, extracted with EA, washed with water and brine, dried and concentrated, purified on TLC (CH2Cl2:MeOH=30:1) to give yellow solid. MS (m/z): 496 (M+H)+

Workup

  1. extractionextracted with EA
  2. washwashed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. custompurified on TLC (CH2Cl2:MeOH=30:1)
  6. customto give yellow solid

Sources & evidence

ORD record
ord-f8011d936ea747b686b9484f4b59fca1
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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