Dichloromethane → HCID 66830588, compound

HRID 1687877Notes

Reaction equation

HRID 1687877 reaction equation
[Cl:1][C:2]1[C:3]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[S:32]([N:35]([CH3:37])[CH3:36])(=[O:34])=[O:33])=[N:4][C:5]([NH:8][C:9]2[C:22]([O:23][CH3:24])=[CH:21][C:12]3[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][OH:20])[CH2:16][CH2:17][C:11]=3[CH:10]=2)=[N:6][CH:7]=1.C(Cl)Cl.C(N(CC)CC)C.[C:48](Cl)(=[O:51])[CH2:49][CH3:50]>>[Cl:1][C:2]1[C:3]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[S:32](=[O:34])(=[O:33])[N:35]([CH3:36])[CH3:37])=[N:4][C:5]([NH:8][C:9]2[C:22]([O:23][CH3:24])=[CH:21][C:12]3[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][O:20][C:48](=[O:51])[CH2:49][CH3:50])[CH2:16][CH2:17][C:11]=3[CH:10]=2)=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 66830352HCID 66830352, compound

Product 1

HCID 66830588HCID 66830588, compound

Procedure

2-{5-Chloro-2-[3-(2-hydroxy-ethyl)-8-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamino]-pyrimidin-4-ylamino}-N,N-dimethyl-benzenesulfonamide (80.0 mg, 0.146 mmol) was stirred in Methylene chloride (1.60 mL, 25.0 mmol) with Triethylamine (30.6 μL, 0.219 mmol) at room temperature. Propanoyl chloride (12.7 μL, 0.146 mmol) was then added quickly under nitrogen. The reaction was complete after stirring over night. The reaction mixture was washed with bicarb and extracted with XS DCM. The organic layer was dried over MgSO4 and filtered. The filtrate was chromatographed on an ISCO flash system (0-10% MeOH:DCM). The desired fractions were concentrated and the product was obtained as a foam from a small amount of DCM (35 mg, 40%). mp: 40° C. softened, 60-70 glass, MS (ESI+): 603 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 9.35 (s, 1H), 8.54 (d, J=8 Hz, 1H), 8.16 (s, 1H), 8.01 (s, 1H), 7.90 (d, J=8 Hz, 1H), 7.57 (t, 1H), 7.51 (s, 1H), 7.25 (m, 1H), 6.67 (s, 1H), 4.25 (t, J=6 Hz, 2H), 3.89 (s, 3H), 2.87 (m, 2H), 2.83 (t, J=6 Hz, 2H), 2.76-2.72 (m, 12H), 2.36 (t, J=7.5 Hz, 2H), 1.17 (t, J=7.5, 3H).

Workup

  1. washThe reaction mixture was washed with bicarb
  2. extractionextracted with XS DCM
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was chromatographed on an ISCO flash system (0-10% MeOH:DCM)
  6. concentrationThe desired fractions were concentrated
  7. customthe product was obtained as a foam from a small amount of DCM (35 mg, 40%)

Sources & evidence

ORD record
ord-ea280f9cdc294942a58427f01a5d87d9
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…