Tetrahydrofuran → HCID 66830067, compound

HRID 1040917Notes

Reaction equation

HRID 1040917 reaction equation
Cl.[Cl:2][C:3]1[C:4]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[N:5][C:6]([NH:9][C:10]2[CH:11]=[CH:12][C:13]3[CH2:19][NH:18][CH2:17][CH2:16][N:15]([CH3:20])[C:14]=3[CH:21]=2)=[N:7][CH:8]=1.Br[CH2:35][C:36]([O:38][CH3:39])=[O:37].O1CCCC1.CCN(C(C)C)C(C)C>CO.ClCCl>[CH3:39][O:38][C:36](=[O:37])[CH2:35][N:18]1[CH2:19][C:13]2[CH:12]=[CH:11][C:10]([NH:9][C:6]3[N:5]=[C:4]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[NH:29][S:30]([CH3:33])(=[O:31])=[O:32])[C:3]([Cl:2])=[CH:8][N:7]=3)=[CH:21][C:14]=2[N:15]([CH3:20])[CH2:16][CH2:17]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 67263416HCID 67263416, compound

Product 1

HCID 66830067HCID 66830067, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To 40 ml sure-seal reaction vial, N-{2-[5-Chloro-2-(1-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-pyrimidin-4-ylamino]-phenyl}-methanesulfonamide hydrochloride (53 mg, 0.11 mmole), methyl bromoacetate (0.010 ml, 0.11 mmole), tetrahydrofuran (5 ml), and Hunig's base (0.2 ml, 1.2 mmoles) were added. The reaction was then heated to 70 C for 5 hours. The solvent was then removed under vacuum. The product (25 mg, 41% yield) was isolated via column chromatography with dichloromethane and methanol as eluant. NMR 1H-(CDCl3)-δ-8.04 (s, 1H), 7.74 (d, 1H, J=7.33 Hz), 7.61 (s, 1H), 7.46 (d, 1H, J=7.08 Hz), 7.02-7.35 (m, 3H), 7.07 (s, 1H), 6.92 (d, 1H, J=8.34 Hz), 6.86 9d, 1H, J=8.08 Hz), 6.82 (s, 1H), 3.83 (s, 2H), 3.75 (s, 3H), 3.30 (s, 2H), 3.02 (bd, 2H, J=4.65 Hz), 2.96 (bd, 2H, J=5.31 Hz), 2.91 (s, 3H), 2.69 (s, 3H). LCMS (ESI+) 546.31 (M+H); MP=106-124° C.

Workup

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

Sources & evidence

ORD record
ord-14cfa16af4a54b8994db9ff05316e9b9
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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