Dimethylformamide → HCID 67263814, compound

HRID 1040919Notes

Reaction equation

HRID 1040919 reaction equation
[Cl:1][C:2]1[C:3]([NH:21][C@@H:22]2[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]2[NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[CH2:18][NH:17][CH2:16][CH2:15][N:14]([CH3:19])[C:13]=3[CH:20]=2)=[N:6][CH:7]=1.[C:33]([O:36][CH2:37][CH2:38]Br)(=[O:35])[CH3:34].C(N(CC)CC)C.CN(C=O)C>CO.ClCCl>[Cl:1][C:2]1[C:3]([NH:21][C@@H:22]2[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]2[NH:28][S:29]([CH3:32])(=[O:30])=[O:31])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[CH2:18][N:17]([CH2:38][CH2:37][O:36][C:33](=[O:35])[CH3:34])[CH2:16][CH2:15][N:14]([CH3:19])[C:13]=3[CH:20]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 135641-Acetoxy-2-bromoethaneHCID 67263327HCID 67263327, compound

Product 1

HCID 67263814HCID 67263814, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To 40 ml sure-seal reaction vial, N-{(1R,2R)-2-[5-chloro-2-(1-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-pyrimidin-4-ylamino]-cyclohexyl}-methanesulfonamide (90 mg, 0.19 mmole), 2-bromoethyl acetate (36 mg, 0.21 mmole), triethylamine (0.3 ml, 2.1 mmoles), KI (10 mg, catalytic), and DMF (5 ml) were added. The reaction was heated to 70 C for 18 hours. The solvent was removed under vacuum to afford a brown solid. The desired product (64 mg, 54% yield) was isolated via column chromatography with dichloromethane and methanol as eluant. NMR 1H-(CDCl3)-δ-7.94 (s, 1H), 7.16 (d, 1H, J=7.58 Hz), 7.06 (d, 1H, J=8.08 Hz), 6.93 (s, 1H), 6.83 (s, 1H), 5.37 (d, 1H, J=7.58 Hz), 5.31 (d, 1H, J=7.58 Hz), 4.20 (t, 2H, J=5.81 Hz), 3.85-4.00 (m, 3H), 3.15-3.30 (m, 1H), 2.95-3.10 (m, 4H), 2.91 (s, 3H), 2.78 (s, 3H), 2.70 (t, 2H, J=6.13 Hz), 2.12-2.25 (m, 2H), 2.07 (s, 3H), 1.78-1.90 (m, 2H), 1.30-1.50 (m, 4H) LCMS (ESI+) 566.41 (M+H); MP=110-142° C.

Workup

  1. customTo 40 ml sure-seal
  2. customreaction vial
  3. temperatureThe reaction was heated to 70 C for 18 hours
  4. customThe solvent was removed under vacuum
  5. customto afford a brown solid

Sources & evidence

ORD record
ord-aefa0c19244541458d5e0d4d3e8e7ce1
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…