1-(Chloromethoxy)-2-methoxyethane → HCID 68486204, compound

HRID 1428884Notes

Reaction equation

HRID 1428884 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[NH:20][C:19](=[O:21])[C:18]3[C:13](=[CH:14][C:15]([I:22])=[CH:16][CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])[CH3:2].CCN(C(C)C)C(C)C.Cl[CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:20]([CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])[C:19](=[O:21])[C:18]3[C:13](=[CH:14][C:15]([I:22])=[CH:16][CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 136337190HCID 136337190, compound

Product 1

HCID 68486204HCID 68486204, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-(7-iodo-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (1.65 g, 4.02 mmol) and THF (20 mL) was added DIPEA (2.10 mL, 12.1 mmol) followed by 1-chloromethoxy-2-methoxy-ethane (1.01 mL, 8.85 mmol) at 23° C. After stirring for 18 h, the reaction mixture was concentrated under reduced pressure. The residue was used in subsequent reactions without further purification (1.89 g, 94%). MS (ESI): mass calcd. for C18H19IN4O5, 498.0; m/z found, 499.0 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 8.85 (d, J=0.6 Hz, 1H), 8.30 (d, J=0.6 Hz, 1H), 8.17 (d, J=1.4 Hz, 1H), 8.00 (dd, J=8.3, 1.6 Hz, 1H), 7.95 (d, J=8.3 Hz, 1H), 5.65 (s, 2H), 4.30 (q, J=7.1 Hz, 2H), 3.50-3.48 (m, 2H), 3.26-3.23 (m, 2H), 3.05 (s, 3H), 1.31 (t, J=7.1 Hz, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was used in subsequent reactions without further purification (1.89 g, 94%)

Sources & evidence

ORD record
ord-6e3864444c53412bbad516aa63d2bff5
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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