Water → tert-butyl 2-acetamido-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate

HRID 39361Notes

Reaction equation

HRID 39361 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:5][N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:8][C:9]=2[N:10]=1.[C:18](Cl)(=[O:20])[CH3:19].O>N1C=CC=CC=1>[C:18]([NH:1][C:2]1[S:3][C:4]2[CH2:5][N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:8][C:9]=2[N:10]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 11357283tert-butyl 2-amino-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridine-5-carboxylate

Product 1

HCID 47146196tert-butyl 2-acetamido-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

As shown in step 10-ii of Scheme 10, to Compound 1033 (10.0 g) in pyridine (80 mL) was added acetyl chloride (4.2 mL). After stirring at 50° C. for 30 min, water (200 mL) was added. The resulting solid was collected by filtration and washed with water (2×) gave tert-butyl 2-acetamido-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (Compound 1034, 10.873 g).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with water (2×)

Sources & evidence

ORD record
ord-86a05d7862404684a1143e751007b1c9
Source dataset
uspto-grants-2013_09
Patent number
US08524906B2

Reaction notes

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