Dimethylamine, hydrochloride → HCID 90204424, compound

HRID 624880Notes

Reaction equation

[C:1]([N:5]([CH2:25][C:26](O)=[O:27])[C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:17][C:16]([F:19])([F:18])[CH2:15]2)=[C:10]([O:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)[N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:30][NH:31][CH3:32].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>>[C:1]([N:5]([CH2:25][C:26](=[O:27])[N:31]([CH3:32])[CH3:30])[C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:17][C:16]([F:19])([F:18])[CH2:15]2)=[C:10]([O:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)[N:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 4

HCID 10473Dimethylamine, hydrochloride

HCID 81531Diisopropylethylamine

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

HCID 76283582HCID 76283582, compound

Product 1

HCID 90204424HCID 90204424, compound

Procedure

In analogy to the procedure described in Example 47 b), {tert-butyl-[6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carbonyl]-amino}-acetic acid (Example 24) was reacted with dimethylamine hydrochloride (CAN 506-59-2) in the presence of TBTU and DIEA to obtain the title compound as colorless oil; MS (EI): m/e=425.5 [MH+].

Sources & evidence

ORD record: ord-48f5a2bed4cf4eae8bf769bd259fddc9
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303012B2

Reaction notes

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