Tetrahydrofuran → HCID 66830067, compound

HRID 1687225Notes

Reaction equation

HRID 1687225 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 7{tilde over (0)} 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), 0 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).

Workup

  1. customTo 40 ml sure-seal
  2. customreaction vial
  3. customThe solvent was then removed under vacuum

Sources & evidence

ORD record
ord-8230c6d133fd4a468c71ba15bb1b5a9f
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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