Methanol → HCID 71657446, compound

HRID 591356Notes

Reaction equation

HRID 591356 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]([NH:19][C:20]3[S:21][C:22]4[CH2:23][NH:24][CH2:25][CH2:26][C:27]=4[N:28]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:35](Cl)(=[O:37])[CH3:36].CO>C(Cl)Cl>[C:35]([N:24]1[CH2:25][CH2:26][C:27]2[N:28]=[C:20]([NH:19][C:17]([N:14]3[CH2:13][CH2:12][CH:11]([N:8]4[C:9]5[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=5)[CH2:6][CH2:7]4)[CH2:16][CH2:15]3)=[O:18])[S:21][C:22]=2[CH2:23]1)(=[O:37])[CH3:36]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 6367Acetyl chlorideHCID 71657445HCID 71657445, compound

Product 1

HCID 71657446HCID 71657446, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(6-fluoroindolin-1-yl)-N-(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)piperidine-1-carboxamide, prepared as in Example 19 above (51.6 mg, 0.1 mmol) in CH2Cl2 (2 mL) was added pyridine (0.5 mL) and then acetyl chloride (0.014 mL, 0.2 mmol, 2 equiv) at room temperature. The resulting mixture was stirred at room temperature for 15 min and then MeOH (1 mL) was added. The resulting mixture was continuously stirred for 15 min and concentrated. The resulting residue was purified by column using EtOAc as the eluent to yield N-(5-acetyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)-4-(6-fluoroindolin-1-yl)piperidine-1-carboxamide.

Workup

  1. customat room temperature
  2. stirringThe resulting mixture was continuously stirred for 15 min
  3. concentrationconcentrated
  4. customThe resulting residue was purified by column

Sources & evidence

ORD record
ord-302774fcab8642e7a2a90267998c3cd2
Source dataset
uspto-grants-2016_01
Patent number
US09238658B2

Reaction notes

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