Pyridine → HCID 67442475, compound

HRID 1400926Notes

Reaction equation

HRID 1400926 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[S:23][C:22]4[C:17](=[N:18][CH:19]=[CH:20][C:21]=4[O:24][C:25]4[CH:30]=[CH:29][C:28]([NH:31][C:32]([NH:34][CH:35]5[CH2:37][CH2:36]5)=[O:33])=[CH:27][C:26]=4[F:38])[CH:16]=3)=[N:13][CH:14]=2)[CH2:4][CH2:3]1.N1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.Cl[C:46]([O-:48])=[O:47].[CH3:49]N1C(=O)CCC1>>[CH:35]1([NH:34][C:32](=[O:33])[NH:31][C:28]2[CH:29]=[CH:30][C:25]([O:24][C:21]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:16]=[C:15]([C:12]5[N:13]=[CH:14][C:9]([CH2:8][N:5]6[CH2:6][CH2:7][CH:2]([NH:1][C:46](=[O:47])[O:48][C:40]7[CH:49]=[CH:44][CH:43]=[CH:42][CH:41]=7)[CH2:3][CH2:4]6)=[CH:10][CH:11]=5)[S:23][C:22]=34)=[C:26]([F:38])[CH:27]=2)[CH2:36][CH2:37]1

Participants

5

Reactant 4

HCID 1049PyridineHCID 13387N-methyl-2-pyrrolidoneHCID 21226386CarbonochloridateHCID 67443027HCID 67443027, compound

Product 1

HCID 67442475HCID 67442475, compoundYield 47.9%

Conditions

Temperature
0 °C

Procedure

To a solution of the amine 343 (0.9 g, 1.69 mmol) in NMP (10 mL) at 0° C. was added pyridine (0.3 ml, 3.71 mmol) followed by the chloroformate (0.3 mL, 2.38 mmol). The mixture was stirred for 40 min at 0° C. then at room temperature for 120 min, quenched by addition of brine/NaHCO3 solution. A precipitate was formed which was collected by filtration and dried. The crude material was purified by flash column chromatography, eluent a 5 to 10% gradient of MeOH (containing 2% ammonia) in DCM, to afford the title compound 356 (0.528 g, 47.9% yield). MS (m/z): 653.6 (M+1)+.

Workup

  1. waitat room temperature for 120 min
  2. customquenched by addition of brine/NaHCO3 solution
  3. customA precipitate was formed which
  4. filtrationwas collected by filtration
  5. customdried
  6. customThe crude material was purified by flash column chromatography, eluent a 5 to 10% gradient of MeOH (containing 2% ammonia) in DCM

Sources & evidence

ORD record
ord-f5557acacd3d41be9765541fd1507c52
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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