Procaine hydrochloride → HCID 67029326, compound

HRID 404431Notes

Reaction equation

[N:1]1([C:7]2[N:12]=[C:11]([N:13]3[CH:18]4[CH2:19][CH2:20][CH:14]3[CH2:15][O:16][CH2:17]4)[N:10]=[C:9]([C:21]3[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:40][CH2:41][N:42]([CH2:45][CH2:46][O:47][C:48]([C:50]1[CH:51]=[CH:52][C:53]([NH2:56])=[CH:54][CH:55]=1)=[O:49])[CH2:43][CH3:44].Cl>>[N:1]1([C:7]2[N:12]=[C:11]([N:13]3[CH:14]4[CH2:20][CH2:19][CH:18]3[CH2:17][O:16][CH2:15]4)[N:10]=[C:9]([C:21]3[CH:27]=[CH:26][C:24]([NH:25][C:29]([NH:56][C:53]4[CH:54]=[CH:55][C:50]([C:48]([O:47][CH2:46][CH2:45][N:42]([CH2:41][CH3:40])[CH2:43][CH3:44])=[O:49])=[CH:51][CH:52]=4)=[O:31])=[CH:23][CH:22]=3)[N:8]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

Reactant 3

HCID 5795Procaine hydrochloride

HCID 94429Triphosgene

HCID 670216444-[4-Morpholin-4-yl-6-(3-oxa-8-azabicyclo[3.2.1]oct-8-yl)-1,3,5-triazin-2-yl]aniline

Product 1

HCID 67029326HCID 67029326, compoundYield 38.6%

Procedure

Following the procedure described in example 34, reaction of 4-[4-morpholin-4-yl-6-(3-oxa-8-azabicyclo[3.2.1]oct-8-yl)-1,3,5-triazin-2-yl]aniline (22 mg, 0.06 mmol) (22 mg, 0.06 mmol, triphosgene (18 mg, 0.06 mmol) and procaine hydrochloride (50 mg, 0.18 mmol) gave the title compound as off-white solid (1TFA salt, 14.6 mg, 33% yield). MS (ESI) m/z 613.6.

Sources & evidence

ORD record: ord-0f57daeaff474d7eabbf41227ffe2e23
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748421B2

Reaction notes

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