Triethylamine → HCID 90386067, compound

HRID 2274861Notes

Reaction equation

Cl.[CH3:2][C:3]([C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1)([CH3:6])[CH2:4][NH2:5].C(N(CC)CC)C.ClC(Cl)(O[C:25](=[O:31])OC(Cl)(Cl)Cl)Cl.FC(F)(F)C(O)=O.[CH3:40][C:41]1([NH2:49])[CH:46]2[CH2:47][CH2:48][N:43]([CH2:44][CH2:45]2)[CH2:42]1>>[CH3:6][C:3]([C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1)([CH3:2])[CH2:4][NH:5][C:25]([NH:49][C:41]1([CH3:40])[CH:46]2[CH2:47][CH2:48][N:43]([CH2:44][CH2:45]2)[CH2:42]1)=[O:31]

Participants

Reactant 4

HCID 8471Triethylamine

HCID 94429Triphosgene

HCID 68327616HCID 68327616, compound

HCID 90386716HCID 90386716, compound

Product 1

HCID 90386067HCID 90386067, compoundYield 69.1%

Procedure

Using general procedure D, 2-methyl-2-(m-tolyl)propan-1-amine hydrochloride (100 mg, 0.501 mmol), triethylamine (279 uL, 2.00 mmol), triphosgene (47 mg, 0.18 mmol) and 3-methylquinuclidin-3-amine 2,2,2-trifluoroacetate (140 mg, 0.550 mmol) gave 1-(2-methyl-2-(m-tolyl)propyl)-3-(3-methylquinuclidin-3-yl)urea (41 mg, 25%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.23 (t, J=7.7 Hz, 1H), 7.18-7.12 (m, 2H), 7.04 (d, J=7.5 Hz, 1H), 4.12 (s, 1H), 4.08 (t, J=6.0 Hz, 1H), 3.39-3.22 (m, 2H), 2.81-2.62 (m, 6H), 2.34 (s, 3H), 1.98-1.89 (m, 1H), 1.80-1.63 (m, 2H), 1.51-1.23 (m, J=26.9 Hz, 2H), 1.37 (s, 3H), 1.30 (s, 6H) ppm. 13C NMR (100 MHz, CDCl3) δ 157.9, 147.1, 138.2, 128.6, 127.1, 127.1, 123.3, 64.0, 52.2, 52.1, 46.9, 46.7, 39.2, 31.2, 27.1, 26.8, 25.4, 23.5, 22.7, 21.9. Purity: >99.9% UPLCMS (210 nm); retention time 0.79 min; (M+1) 330.

Sources & evidence

ORD record: ord-bb5ba0432e284b3784cdf881539c7edf
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126993B2

Reaction notes

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