Triethylamine → HCID 71062870, compound

HRID 1524183Notes

Reaction equation

HRID 1524183 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.[NH:13]1[CH2:18][CH2:17][O:16][CH:15]([CH2:19][OH:20])[CH2:14]1.C(N(CC)CC)C>C(#N)C>[N:4]1([CH2:3][CH2:2][N:13]2[CH2:18][CH2:17][O:16][C@H:15]([CH2:19][OH:20])[CH2:14]2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3497988Morpholin-2-ylmethanol2×HCID 52984061HCID 52984061, compound2×

Product 1

HCID 71062870HCID 71062870, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A microwave vial was charged with 1-(chloroethyl)-indoline (compound 50; 724 mg, 4.00 mmol), hydroxymethylmorpholine (compound 54; 562 mg, 4.80 mmol), triethylamine (2.2 ml, 16.00 mmol) and acetonitrile (4 ml). The vial was irradiated with microwaves for 2 hrs at 100° C., 40 min at 120° C. and 1 hr at 110° C. The residue was purified by flash column chromatography (silica, DCM/MeOH 1:0 to 8:2); and the product was isolated as an off-white solid (347 mg; 33%).

Workup

  1. customThe vial was irradiated with microwaves for 2 hrs at 100° C., 40 min at 120° C. and 1 hr at 110° C
  2. customThe residue was purified by flash column chromatography (silica, DCM/MeOH 1:0 to 8:2)
  3. customand the product was isolated as an off-white solid (347 mg; 33%)

Sources & evidence

ORD record
ord-f9ec007611a04448abe442d82b893156
Source dataset
uspto-grants-2015_07
Patent number
US09079895B2

Reaction notes

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