Isopropyl chloroformate → HCID 85472051, compound

HRID 713696Notes

Reaction equation

HRID 713696 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[O:10][C:9]([C:11]3[CH:12]=[C:13]([NH:18][C:19]([C:21]4[O:22][CH:23]=[CH:24][CH:25]=4)=[O:20])[CH:14]=[CH:15][C:16]=3[Cl:17])=[N:8][C:5]2=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[C:34]([O:36][CH:37]([CH3:39])[CH3:38])=[O:35]>ClCCl>[Cl:17][C:16]1[CH:15]=[CH:14][C:13]([NH:18][C:19]([C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)=[O:20])=[CH:12][C:11]=1[C:9]1[O:10][C:4]2[C:5]([N:8]=1)=[N:6][CH:7]=[C:2]([NH:1][C:34](=[O:35])[O:36][CH:37]([CH3:39])[CH3:38])[CH:3]=2

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 90411377HCID 90411377, compound

Product 1

HCID 85472051HCID 85472051, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of N-(3-[6-amino-[1,3]oxazolo[4,5-b]pyridin-2-yl]-4-chlorophenyl)furan-2-carboxamide (1-15) (100 mg, 0.28 mmol, 1.00 equiv), triethylamine (85 mg, 0.84 mmol, 2.98 equiv), chloro(propan-2-yloxy)methanone (70 mg, 0.57 mmol, 2.03 equiv) in dichloromethane (15 mL). The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (10:1). This resulted in 10 mg (8%) of propan-2-yl N-[2-[2-chloro-5-(furan-2-amido)phenyl]-[1,3]oxazolo[4,5-b]pyridin-6-yl]carbamate (76) as a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThis resulted in 10 mg (8%) of propan-2-yl N-[2-[2-chloro-5-(furan-2-amido)phenyl]-[1,3]oxazolo[4,5-b]pyridin-6-yl]carbamate (76) as a yellow solid

Sources & evidence

ORD record
ord-23435b77bd774c42af16d25349d64dc2
Source dataset
uspto-grants-2015_11
Patent number
US09186361B2

Reaction notes

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