Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 86634072, compound

HRID 1041713Notes

Reaction equation

HRID 1041713 reaction equation
C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.Cl[C:17]1[N:22]=[C:21]([NH:23][C:24]2[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:25]=2[C:26]([NH:28][CH2:29][C:30]#[CH:31])=[O:27])[C:20]([Cl:37])=[CH:19][N:18]=1.[NH2:38][C:39]1[CH:54]=[CH:53][C:42]2[N:43]([CH2:51][CH3:52])[CH2:44][C:45]([CH2:49][OH:50])([OH:48])[CH2:46][O:47][C:41]=2[CH:40]=1>C(O)(C)C>[Cl:37][C:20]1[C:21]([NH:23][C:24]2[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:25]=2[C:26]([NH:28][CH2:29][C:30]#[CH:31])=[O:27])=[N:22][C:17]([NH:38][C:39]2[CH:54]=[CH:53][C:42]3[N:43]([CH2:51][CH3:52])[CH2:44][C:45]([OH:48])([CH2:49][OH:50])[CH2:46][O:47][C:41]=3[CH:40]=2)=[N:18][CH:19]=1

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 67264302HCID 67264302, compoundHCID 866339022-(2,5-Dichloro-pyrimidin-4-ylamino)-3-fluoro-N-prop-2-ynyl-benzamide

Product 1

HCID 86634072HCID 86634072, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

10-Camphorsulfonic acid (107 mg, 0.462 mmol), 2-(2,5-Dichloro-pyrimidin-4-ylamino)-3-fluoro-N-prop-2-ynyl-benzamide (142 mg, 0.420 mmol), and 3-Amino-9-ethyl-7-hydroxymethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-ol (0.100 g, 0.420 mmol) in Isopropyl alcohol (3.0 mL) and the mixture was irradiated in a CEM microwave (120° C., 40 min). The reaction mixture was then purified by HPLC and lyophilized to afford 2-[5-Chloro-2-(9-ethyl-7-hydroxy-7-hydroxymethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamino)-pyrimidin-4-ylamino]-3-fluoro-N-prop-2-ynyl-benzamide as a yellow lyophilate (2 mg, 1%). LCMS: 541.31 (M+H); HNMR (CDCl3): 9.33 (s, 1H), 8.02 (s, 1H), 7.46 (d, J=5.32 Hz, 4H), 7.33 (s, 1H), 6.97 (s, 1H), 6.65 (d, J=7.80 Hz, 1H), 4.05 (m, 4H), 3.87 (s, 2H), 3.51 (s, 2H), 3.13 (s, 2H), 1.12 (t, J=7.04 Hz, 3H);

Workup

  1. customThe reaction mixture was then purified by HPLC

Sources & evidence

ORD record
ord-d10aa938e33943939875fa3c3a601cd6
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…