Propargyl bromide → 4-(2-Propyn-1-yl)morpholine

HRID 1064205Notes

Reaction equation

CO[C:3]([C:5]1[NH:6][C:7]2[CH:8]=[C:9]([NH:19][C:20]([O:22]C(C)(C)C)=O)[CH:10]=[C:11]3[C:17](=[O:18])[NH:16][N:15]=[CH:14][C:13]=1[C:12]=23)=O.[CH2:27]([N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)[C:28]#[CH:29].Br[CH2:37][C:38]#[CH:39].N1[CH2:45][CH2:44]OCC1.C([O-])([O-])=O.[K+].[K+].O1[CH2:56][CH2:55][CH2:54][CH2:53]1>>[CH2:27]([N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)[C:28]#[CH:29].[N:30]1([CH2:27][C:28]#[C:3][C:5]2[NH:6][C:7]3[CH:8]=[C:9]([NH:19][C:20]([C@@H:38]4[CH2:39][C@H:37]4[C:45]4[CH:44]=[CH:56][CH:55]=[CH:54][CH:53]=4)=[O:22])[CH:10]=[C:11]4[C:17](=[O:18])[NH:16][N:15]=[CH:14][C:13]=2[C:12]=34)[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Participants

Reactant 6

HCID 7842Propargyl bromide

HCID 8028Tetrahydrofuran

HCID 8083Morpholine

HCID 11430Potassium Carbonate

HCID 4129414-(2-Propyn-1-yl)morpholine

HCID 1361816128-tert-Butoxycarbonylamino-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indole-2-carboxylic acid methyl ester

Product 2

HCID 4129414-(2-Propyn-1-yl)morpholine

HCID 136141607(1r,2r)-2-Phenyl-cyclopropanecarboxylic acid [2-(3-morpholin-4-yl-prop-1-ynyl)-6-oxo-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl]-amide

Procedure

Preparation of example 246 from Intermediate 147(d) of Example 147 (300 mg, 0.794 mmol) was carried out in three steps in a manner similar to that described for the preparation of Example 233 except that 4-prop-2-ynyl-morpholine was used instead of dimethyl-prop-2-ynyl-amine in step 1. 4-Prop-2-ynyl-morpholine was prepared by refluxing 3-bromo-propyne, morpholine and K2CO3 in tetrahydrofuran for 1 hour. The title compound (34 mg, 0.073 mmol) was obtained as a yellow powder in 18% overall yield.

Sources & evidence

ORD record: ord-7f086cc57d144a7a98774858988e4768
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06967198B2

Reaction notes

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