Pyridine → HCID 86726652, compound

HRID 1499395Notes

Reaction equation

HRID 1499395 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[N:11][C:10]=1[C:22]([OH:24])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(N(C)C)=C(C)C.[NH2:33][C:34]1[CH:35]=[N:36][C:37]2[C:42]([C:43]=1[N:44]1[CH2:49][CH2:48][CH2:47][C@H:46]([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])[CH2:45]1)=[CH:41][CH:40]=[CH:39][CH:38]=2.N1C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:14]2[C:15]([F:21])=[CH:16][CH:17]=[CH:18][C:19]=2[F:20])=[N:11][C:10]=1[C:22]([NH:33][C:34]1[CH:35]=[N:36][C:37]2[C:42]([C:43]=1[N:44]1[CH2:49][CH2:48][CH2:47][C@H:46]([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:55])([CH3:54])[CH3:56])[CH2:45]1)=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:24])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 674381985-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acidHCID 86726649HCID 86726649, compound

Product 1

HCID 86726652HCID 86726652, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 5-[(tert-butoxycarbonyl)amino]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxylic acid (81.1 mg, 0.228 mmol) in THF (0.5 mL), a solution of 1-chloro-N,N,2-trimethylpropenylamine (Aldrich, 80.5 mg, 0.602 mmol) in THF (1.0 mL) was added. The mixture was stirred at room temperature for 5 h. To the above mixture was added a solution of tert-butyl [(3S)-1-(3-aminoquinolin-4-yl)piperidin-3-yl]carbamate (63.8 mg, 0.186 mmol) in THF (2.0 mL) followed by pyridine (146.4 mg, 1.851 mmol). The mixture was stirred at room temperature for 2 h, and then concentrated under reduced pressure. The resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes) to afford the sub-title compound as a yellow solid (115.8 mg, 91%). LCMS calc. for C34H39F2N6O5S (M+H)+: m/z=681.3. found 681.3.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 h
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6cbea7e556614811a313eb561dabc453
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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