4-Methylmorpholine → HCID 59577391, compound

HRID 1947542Notes

Reaction equation

HRID 1947542 reaction equation
Cl.Cl.[CH2:3]1[CH:7]2[CH2:8][NH:9][CH2:10][CH:6]2[CH2:5][N:4]1[CH2:11][C:12]1[C:16]2[CH:17]=[CH:18][C:19]([O:21][C:22]3[S:23][C:24]4[C:25]([N:30]=3)=[N:26][CH:27]=[CH:28][CH:29]=4)=[CH:20][C:15]=2[O:14][CH:13]=1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[O:48]1[CH2:52][CH2:51][CH:50]([C:53](O)=[O:54])[CH2:49]1>CN(C=O)C>[O:48]1[CH2:52][CH2:51][CH:50]([C:53]([N:9]2[CH2:10][CH:6]3[CH:7]([CH2:3][N:4]([CH2:11][C:12]4[C:16]5[CH:17]=[CH:18][C:19]([O:21][C:22]6[S:23][C:24]7[C:25]([N:30]=6)=[N:26][CH:27]=[CH:28][CH:29]=7)=[CH:20][C:15]=5[O:14][CH:13]=4)[CH2:5]3)[CH2:8]2)=[O:54])[CH2:49]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 4661317(R)-Tetrahydro-3-furoic acidHCID 68771555HCID 68771555, compound

Product 1

HCID 59577391HCID 59577391, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[3-(hexahydro-pyrrolo[3,4-c]pyrrol-2-ylmethyl)-benzofuran-6-yloxy]-thiazolo[4,5-b]pyridine dihydrochloride (50 mg, 0.11 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbdiimide hydrochloride (21 mg, 0.11 mmol), 1-hydroxybenzotriazole (73 mg, 0.54 mmol), N-methylmorpholine (33 mg, 0.32 mmol), and tetrahydro-furan-3-carboxylic acid (13 mg, 0.11 mmol) in DMF (0.4 mL) was stirred at rt. Upon reaction completion, the mixture was concentrated, re-dissolved in DMF and purified using reverse phase HPLC to provide the title compound (24 mg, 45%). MS (ESI): mass calculated for C26H26N4O4S, 490.17; m/z found, 491.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.56 (dd, J=4.8, 1.6, 1H), 8.03 (dd, J=8.0, 1.5, 1H), 7.70 (dd, J=8.5, 2.9, 1H), 7.59 (dd, J=5.6, 3.4, 2H), 7.27-7.18 (m, 2H), 4.08-3.95 (m, 1H), 3.94-3.60 (m, 7H), 3.53-3.42 (m, 1H), 3.40-3.26 (m, 1H), 3.17-3.06 (m, 1H), 2.99-2.77 (m, 2H), 2.71-2.46 (m, 4H), 2.29-2.14 (m, 1H), 2.14-1.99 (m, 1H).

Workup

  1. customUpon reaction completion
  2. concentrationthe mixture was concentrated
  3. dissolutionre-dissolved in DMF
  4. custompurified

Sources & evidence

ORD record
ord-12adb01b1882495da3d696d9975799d8
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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