Isopropanol → HCID 66829523, compound

HRID 1041477Notes

Reaction equation

HRID 1041477 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[N:10]([CH2:13][CH3:14])[CH2:9][CH2:8][NH:7][C:6]=2[CH:15]=1.Cl[C:17]1[N:22]=[C:21]([NH:23][C:24]2[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([NH:28][CH3:29])=[O:27])[C:20]([Cl:35])=[CH:19][N:18]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(O)(C)C>>[Cl:35][C:20]1[C:21]([NH:23][C:24]2[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([NH:28][CH3:29])=[O:27])=[N:22][C:17]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[C:11](=[O:12])[N:10]([CH2:13][CH3:14])[CH2:9][CH2:8][NH:7][C:6]=3[CH:15]=2)=[N:18][CH:19]=1

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 67264093HCID 67264093, compoundHCID 717421912-(2,5-Dichloropyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide

Product 1

HCID 66829523HCID 66829523, compoundYield 13.5%

Conditions

Temperature
120 °C

Procedure

Into a microwave vial, 8-amino-4-ethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (0.100 g, 0.000487 mol), 2-(2,5-dichloro-pyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide (0.14 g, 0.00046 mol), 10-camphorsulfonic acid (0.22 g, 0.00092 mol) and isopropyl alcohol (1.3 mL, 0.017 mol) were added and heated in the microwave at 120° C. for 40 minutes. The solvent was removed under vacuum. The solid was dissolved in EtOAc and washed with saturated NaHCO3. The organic was separated, washed with Brine, and dried over magnesium sulfate. The solid was filtered and washed with EtOAc. The solvent was removed under vacuum. The product was isolated via Gilson prep-HPLC to give a TFA salt (30 mg, 13%). 1H-NMR (CDCl3, 400 MHz): δ10.97 (bs, 1H), 9.52 (bs, 1H), 7.75 (s, 1H), 7.70 (bs, 1H), 7.28-7.50 m, 4H), 6.90 (d, 1H), 6.28 (bs, 1H), 3.44-3.65 (m, 7H), 3.01 (d, 1H), 1.25 (t, 3H). LC/MS (ESI+) 484.21 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionThe solid was dissolved in EtOAc
  3. washwashed with saturated NaHCO3
  4. customThe organic was separated
  5. washwashed with Brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe solid was filtered
  8. washwashed with EtOAc
  9. customThe solvent was removed under vacuum
  10. customThe product was isolated via Gilson prep-HPLC

Sources & evidence

ORD record
ord-3cbd257131f949c997010f2f0b052acc
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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