Dimethylamine, hydrochloride → HCID 58505613, compound

HRID 1917613Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:18]3[C:13]([CH:14]=[C:15]([CH:19]([CH3:21])[CH3:20])[CH:16]=[CH:17]3)=[C:12]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[C:11]=2[CH2:28][C:29]([CH3:34])([CH3:33])[C:30](O)=[O:31])=[O:9])=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:46]2[N:47]=[CH:48]C=CC=2N=N1.Cl.CNC>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[N:18]3[C:13]([CH:14]=[C:15]([CH:19]([CH3:21])[CH3:20])[CH:16]=[CH:17]3)=[C:12]([C:22](=[O:27])[C:23]([CH3:25])([CH3:26])[CH3:24])[C:11]=2[CH2:28][C:29]([CH3:33])([CH3:34])[C:30]([N:47]([CH3:48])[CH3:46])=[O:31])=[O:9])=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 10473Dimethylamine, hydrochloride

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 58505568HCID 58505568, compound

Product 1

HCID 58505613HCID 58505613, compoundYield 34.2%

Procedure

To a solution of 3-{3-[(4-chlorophenyl)carbonyl]-1-(2,2-dimethylpropanoyl)-7-(propan-2-yl)indolizin-2-yl}-2,2-dimethylpropanoic acid (100 mg, 0.207 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (157.7 mg, 0.415 mmol), and dimethylamine-HCl (18.6 mg, 0.228 mmol) is added TEA (0.173 mL, 1.245 mmol). The reaction is stirred for 16 h then purified by HPLC to give the title compound (36 mg, 34%).

Workup

customthen purified by HPLC

Sources & evidence

ORD record: ord-2204c0b604034fb8bf7b1e71f998194a
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618300B2

Reaction notes

Loading…