Picolinic acid → HCID 10117948, compound

HRID 970926Notes

Reaction equation

[CH3:1][CH2:2][N:3]=[C:4]=[N:5][CH2:6][CH2:7][CH2:8]N(C)C.[N:12]1[C:21]2C(N)CC[CH2:17][C:16]=2[CH:15]=[CH:14][CH:13]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([OH:31])=O.O[N:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2N=N1.C[CH2:43][N:44]([CH:48]([CH3:50])[CH3:49])[CH:45]([CH3:47])C.[CH3:51]N(C=O)C>>[NH:5]1[C:6]2[CH:7]=[CH:8][CH:51]=[CH:1][C:2]=2[N:3]=[C:4]1[CH2:43][N:44]([CH2:45][C:47]1[CH:17]=[C:16]([CH:15]=[CH:14][CH:13]=1)[CH2:21][NH:12][C:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=1)=[O:31])[CH:48]1[C:49]2[N:33]=[CH:37][CH:38]=[CH:39][C:40]=2[CH2:41][CH2:36][CH2:50]1

Participants

Reactant 6

HCID 1018Picolinic acid

HCID 6228Dimethylformamide

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×

HCID 757711-Hydroxybenzotriazole

HCID 81531Diisopropylethylamine

HCID 113555648-Amino-5,6,7,8-tetrahydroquinoline

Product 1

HCID 10117948HCID 10117948, compoundYield 94%

Procedure

Using the EDCI coupling general procedure F: Reaction of (3-aminomethyl-benzyl)-1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (133 mg, 0.33 mmol), picolinic acid (40 mg, 0.33 mmol), 1-hydroxybenzotriazole (45 mg, 0.33 mmol), DIPEA (100 uL, 0.57 mmol), and EDCI (64 mg, 0.33 mmol) in anhydrous DMF (3 mL) for 3 d at room temperature followed by purification of the crude material by chromatography on silica gel (2:2:96 CH3OH—NH3 H2O—CH2Cl2) afforded the title compound (158 mg, 94%) as a white foam.

Workup

customfollowed by purification of the crude material by chromatography on silica gel (2:2:96 CH3OH—NH3 H2O—CH2Cl2)

Sources & evidence

ORD record: ord-f52b2ac021cf4e28ae7c3b3adf81e3d0
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312234B2

Reaction notes

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