Potassium Carbonate → HCID 178523830, compound

HRID 707390Notes

Reaction equation

HRID 707390 reaction equation
CC1C=CC(S(O[C@H:12]2[CH2:15][C@@H:14]([NH:16][C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13]2)(=O)=O)=CC=1.[O:27]1[CH2:32][C:31](=[O:33])[NH:30][C:29]2N=[CH:35][CH:36]=[CH:37][C:28]1=2.[C:38](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(Cl)Cl>[O:33]=[C:31]1[CH2:32][O:27][C:28]2[CH:37]=[CH:36][CH:35]=[CH:38][C:29]=2[N:30]1[C@H:12]1[CH2:13][C@H:14]([NH:16][C:17](=[O:18])[O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:15]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 884992H-pyrido(3,2-b)-1,4-oxazin-3(4H)-oneHCID 178427793HCID 178427793, compound

Product 1

HCID 178523830HCID 178523830, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of cis-3-(((benzyloxy)carbonyl)amino)cyclobutyl 4-methylbenzenesulfonate (0.563 g, 1.5 mmol) in DMF (3.00 ml) was added 2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (FSSI, 0.225 g, 1.500 mmol) and potassium carbonate (EMD, 0.415 g, 3.00 mmol). The resulting mixture was heated to 50° C. overnight. Reaction mixture was heated to 85° C. for 3 hr then at 110° C. overnight. Reaction mixture was diluted with DCM and washed with water and brine. Purification by Biotage (0-10% MeOH/DCM) produced product. Material was advanced to the next step. M+1: 353.9

Workup

  1. customReaction mixture
  2. temperaturewas heated to 85° C. for 3 hr
  3. customat 110° C.
  4. customovernight
  5. customReaction mixture
  6. washwashed with water and brine
  7. customPurification by Biotage (0-10% MeOH/DCM)
  8. customproduced product

Sources & evidence

ORD record
ord-690c6f22928242ca9603ac729cabfe09
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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