Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 53320012, compound

HRID 1688003Notes

Reaction equation

HRID 1688003 reaction equation
C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[CH2:16]([N:18]1[C:24]2[CH:25]=[CH:26][C:27]([NH2:29])=[CH:28][C:23]=2[O:22][CH2:21][CH2:20][CH2:19]1)[CH3:17].Cl[C:31]1[N:36]=[C:35]([NH:37][C:38]2[C:47]([F:48])=[CH:46][CH:45]=[CH:44][C:39]=2[C:40]([NH:42][CH3:43])=[O:41])[C:34]([Cl:49])=[CH:33][N:32]=1>C(O)(C)C>[Cl:49][C:34]1[C:35]([NH:37][C:38]2[C:47]([F:48])=[CH:46][CH:45]=[CH:44][C:39]=2[C:40]([NH:42][CH3:43])=[O:41])=[N:36][C:31]([NH:29][C:27]2[CH:26]=[CH:25][C:24]3[N:18]([CH2:16][CH3:17])[CH2:19][CH2:20][CH2:21][O:22][C:23]=3[CH:28]=2)=[N:32][CH:33]=1

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 672640069-Ethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamineHCID 717421912-(2,5-Dichloropyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide

Product 1

HCID 53320012HCID 53320012, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

10-Camphorsulfonic acid (91 mg, 0.39 mmol) was added to 9-Ethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamine (65 mg, 0.34 mmol) and 2-(2,5-Dichloro-pyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide (110 mg, 0.34 mmol) in Isopropyl alcohol (3 mL). The mixture was irradiated in a CEM microwave (130° C., 40 min). Complete conversion was achieved. The reaction was diluted with 5 mL satd. sodium bicarbonate and the ppt collected. The ppt was purified by ISCO (12 g SiO2, 0-100% EtOAc:Hex) to afford 2-[5-Chloro-2-(9-ethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamino)-pyrimidin-4-ylamino]-3-fluoro-N-methyl-benzamide as a green foam (68 mg, 43%). LCMS: 471 (M+H), 1H-NMR (CDCl3): 8.64 (s, 1H), 8.03 (s, 1H), 7.29 (m, 3H), 7.10 (s, 1H), 6.88 (m, 1H), 6.68 (m, 2H), 6.07 (q, 1H, J=4.5 Hz), 4.03 (t, 2H, J=5.6 Hz), 3.17 (m, 4H), 2.91 (d, 3H, J=4.5 Hz), 1.99 (m, 2H), 1.16 (t, 3H, J=7.0 Hz); 19F-NMR: −112

Workup

  1. customThe mixture was irradiated in a CEM microwave (130° C., 40 min)
  2. additionThe reaction was diluted with 5 mL
  3. customsodium bicarbonate and the ppt collected
  4. customThe ppt was purified by ISCO (12 g SiO2, 0-100% EtOAc:Hex)

Sources & evidence

ORD record
ord-bad849b3caae4a4989c8dec69dd1ee62
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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