Isopropanol → HCID 86633968, compound

HRID 1687537Notes

Reaction equation

HRID 1687537 reaction equation
C(CNC(=O)C1C=CC=C(C)C=1NC1C(Cl)=CN=C(Cl)N=1)#N.[Cl:23][C:24]1[C:25]([NH:45][C:46]2[C:57]([CH3:58])=[CH:56][CH:55]=[CH:54][C:47]=2[C:48]([NH:50][CH2:51][C:52]#[N:53])=[O:49])=[N:26][C:27]([NH:30][C:31]2[CH:44]=[CH:43][C:34]3[NH:35][C:36](=[O:42])[CH2:37][CH2:38][C:39]([CH3:41])([CH3:40])[C:33]=3[CH:32]=2)=[N:28][CH:29]=1.NC1C=CC2NC(=O)CCC(C)(C)C=2C=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(O)(C)C>>[Cl:23][C:24]1[C:25]([NH:45][C:46]2[C:57]([CH3:58])=[CH:56][CH:55]=[CH:54][C:47]=2[C:48]([NH:50][CH2:51][C:52]#[N:53])=[O:49])=[N:26][C:27]([NH:30][C:31]2[CH:44]=[CH:43][C:34]3[NH:35][C:36](=[O:42])[CH2:37][CH2:38][C:39]([CH3:40])([CH3:41])[C:33]=3[CH:32]=2)=[N:28][CH:29]=1

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 578538307-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-oneHCID 86633969HCID 86633969, compound

Product 1

HCID 86633968HCID 86633968, compoundYield 12.4%

Procedure

2-[5-Chloro-2-(5,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamino)-pyrimidin-4-ylamino]-N-cyanomethyl-3-methyl-benzamide N-Cyanomethyl-2-(2,5-dichloro-pyrimidin-4-ylamino)-3-methyl-benzamide (50.0 mg, 0.000149 mol), 7-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (30.4 mg, 0.000149 mol) and 10-Camphorsulfonic acid (34.6 mg, 0.000149 mol) were suspended in Isopropyl alcohol (3.0 mL, 0.039 mol) and the reaction was microwaved on 300 watts, 140° C. for 20 minutes. The reaction mixture was then reduced under nitrogen and the crude residue was isolated and purified by Gilson prep HPLC to afford 9.33 mg (12%) of 2-[5-Chloro-2-(5,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamino)-pyrimidin-4-ylamino]-N-cyanomethyl-3-methyl-benzamide. LC/MS (ESI): 504.15. 1H NMR (400 MHz, DMSO, d6) δ 9.15 (s, 1H), 9.08 (m 1H), 8.93 (m, 1H), 8.80 (m, 1H), 8.11 (s, 1H), 7.50 (m, 2H), 7.34 (m, 3H), 6.61 (d, 1H, J=8.59 Hz), 4.21 (d, 2H, J=5.05 Hz), 2.32 (s, 3H), 2.12 (m, 2H), 1.93 (m, 2H), 1.22 (s, 6H).

Workup

  1. customthe reaction was microwaved on 300 watts, 140° C. for 20 minutes
  2. customthe crude residue was isolated
  3. custompurified by Gilson prep HPLC

Sources & evidence

ORD record
ord-3f09baef88c14327a0a1d97a76949137
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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