Triethylamine → HCID 58997009, compound

HRID 1592677Notes

Reaction equation

HRID 1592677 reaction equation
[Cl:1][C:2]1[CH:10]=[N:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.[NH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:28][N:29]([CH2:40][C:41]2[C:46]([NH2:47])=[CH:45][CH:44]=[CH:43][N:42]=2)[C@@H:30]2[C:39]3[N:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH2:33][CH2:32][CH2:31]2)=[C:24]([CH2:26][OH:27])[CH:25]=1.CCN(CC)CC>C(Cl)Cl.CN(C=O)C.C1COCC1>[NH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:28][N:29]([CH2:40][C:41]2[C:46]([NH:47][C:4](=[O:6])[C:3]3[C:7]([Cl:11])=[CH:8][N:9]=[CH:10][C:2]=3[Cl:1])=[CH:45][CH:44]=[CH:43][N:42]=2)[C@@H:30]2[C:39]3[N:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH2:33][CH2:32][CH2:31]2)=[C:24]([CH2:26][OH:27])[CH:25]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 6057633,5-Dichloroisonicotinic acidHCID 67272664HCID 67272664, compound

Product 1

HCID 58997009HCID 58997009, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 3,5-dichloro-isonicotinic acid (85 mg, 0.44 mmol) in CH2Cl2 (3 mL) was added DMF (1 drop) and oxalyl chloride (0.12 mL, 1.4 mmol). The suspension was stirred at room temperature for 2 h, then concentrated under reduced pressure. A solution of (5-aminomethyl-2-{[(3-amino-pyridin-2-ylmethyl)-((S)-5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenyl)-methanol (88 mg, 0.22 mmol) in THF (3 mL) was added to the acid chloride followed by Et3N (0.04 mL, 0.3 mmol). The mixture was stirred for 1 h, then diluted with CH2Cl2 (10 mL) and washed with water (10 mL). The aqueous layer was extracted with CH2Cl2 (3×8 mL), and the combined organic layers were washed with saturated NaHCO3 (20 mL), then dried (Na2SO4) and concentrated under reduced pressure. The residue was purified using flash chromatography on silica gel (97:2:1 CH2Cl2/MeOH/NH4OH) to give COMPOUND 407 (21 mg, 17%), as a white foam.

Workup

  1. concentrationconcentrated under reduced pressure
  2. stirringThe mixture was stirred for 1 h
  3. washwashed with water (10 mL)
  4. extractionThe aqueous layer was extracted with CH2Cl2 (3×8 mL)
  5. washthe combined organic layers were washed with saturated NaHCO3 (20 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified

Sources & evidence

ORD record
ord-dca971e09d8748d1ad121c9cc4c646c6
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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