Triethylamine → [4-(9H-Pyrimido[4,5-b]indol-4-yl)-morpholin-2-ylmethyl]-carbamic acid tert-butyl ester

HRID 1916282Notes

Reaction equation

Cl[C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:5]=[CH:4][N:3]=1.[C:15]([O:19][C:20](=[O:29])[NH:21][CH2:22][CH:23]1[O:28][CH2:27][CH2:26][NH:25][CH2:24]1)([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>CN(C=O)C>[C:15]([O:19][C:20](=[O:29])[NH:21][CH2:22][CH:23]1[O:28][CH2:27][CH2:26][N:25]([C:2]2[C:14]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[NH:7][C:6]=3[N:5]=[CH:4][N:3]=2)[CH2:24]1)([CH3:18])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-chloro-9H-pyrimido[4,5-b]indole (0.045 g, 0.221 mmol), morpholin-2-ylmethyl-carbamic acid tert-butyl ester (0.055 g, 0.25 mmol) and triethylamine (0.10 mL, 0.75 mmol) in DMF (0.70 mL) was heated to 120° C. in a microwave reactor for 1 hour. The cooled solution was partitioned between water (20 mL) and ethyl acetate (20 mL). The organic extract was dried (Na2SO4), filtered and concentrated. Flash column chromatography, eluting with ethyl acetate, gave the title compound as a yellow solid (0.021 g, 0.0548 mmol, 25%). LC-MS (3) Rt 5.57 min; m/z (ESI) 384 [MH+].

Workup

customThe cooled solution was partitioned between water (20 mL) and ethyl acetate (20 mL)
extractionThe organic extract
dry with materialwas dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
washFlash column chromatography, eluting with ethyl acetate

Sources & evidence

ORD record: ord-7a6c4cdc0c9b4c07ac500df5ec34e625
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618121B2

Reaction notes

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