Hydrochloric Acid → HCID 67263599, compound

HRID 1041527Notes

Reaction equation

HRID 1041527 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[C:5]([Cl:21])=[CH:4][N:3]=1.[CH3:22][O:23][C:24]1[C:25]([NH2:43])=[CH:26][C:27]2[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[CH2:30][CH2:29][C:28]=2[CH:42]=1.Cl>O1CCOCC1.COCCO>[Cl:21][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])=[N:7][C:2]([NH:43][C:25]2[C:24]([O:23][CH3:22])=[CH:42][C:28]3[CH2:29][CH2:30][N:31]([CH2:34][CH2:35][N:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)[CH2:32][CH2:33][C:27]=3[CH:26]=2)=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 597643782,5-dichloro-N-(2-((1-methylethyl)sulfonyl)phenyl)-4-pyrimidinamineHCID 672641368-Methoxy-3-(2-morpholin-4-yl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamine

Product 1

HCID 67263599HCID 67263599, compound

Reagents, catalysts & solvents 2

HCID 80192-MethoxyethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

(2,5-Dichloro-pyrimidin-4-yl)-[2-(propane-2-sulfonyl)-phenyl]-amine (100 mg, 0.289 mmol) and 8-Methoxy-3-(2-morpholin-4-yl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamine (92.6 mg, 0.303 mmol) and 100 μL of 4M HCl in Dioxane (9:1, 1,4-Dioxane:Hydrogen Chloride) in 4 mL of 2-methoxyethanol were heated in a sealed tube at 120° C. over night. The reaction was extracted with DCM and washed with bicarb followed by water. Dried organic layer over MgSO4, filtered and concentrated. The residue was chromatographed on ISCO flash system (0-15% MeOH:DCM). The desired fractions were concentrated and the product was collected as a foam from a small amount of DCM (65 mg, 37%). MS (ESI+): 615 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 9.53 (s, 1H), 8.58 (d, J=8 Hz, 1H), 8.17 (s, 1H), 8.00 (s, 1H), 7.75 (d, J=8 Hz, 1H), 7.62 (t, J=8 Hz, 1H), 7.50 (s, 1H), 7.27 (m, 1H), 6.67 (s, 1H), 3.89 (s, 3H), 3.74 (t, J=4 Hz, 4H), 3.27 (m, 1H), 2.88 (br s, 2H), 2.73-2.69 (m, 8H), 2.58 (m, 2H), 2.52 (br s, 4H), 1.70 (br s, 1H), 1.33 (d, J=7 Hz, 6H).

Workup

  1. extractionThe reaction was extracted with DCM
  2. washwashed with bicarb
  3. filtrationDried organic layer over MgSO4, filtered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on ISCO flash system (0-15% MeOH:DCM)
  6. concentrationThe desired fractions were concentrated
  7. customthe product was collected as a foam from a small amount of DCM (65 mg, 37%)

Sources & evidence

ORD record
ord-9f6d32c399e54703b782a2109fa41453
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…