Benzylamine → HCID 178473319, compound

HRID 1244376Notes

Reaction equation

HRID 1244376 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:9]2[N:10]=[C:11]([C:13]3[NH:14][C:15]4[CH2:20][CH2:19][NH:18][CH2:17][C:16]=4[N:21]=3)[S:12][C:8]=2[C:7]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:6][CH:5]=1.C(N(C(C)C)C(C)C)C.Cl[C:38]([O:40][CH2:41][CH3:42])=[O:39].C(N)C1C=CC=CC=1>O1CCCC1>[CH2:41]([O:40][C:38]([N:18]1[CH2:19][CH2:20][C:15]2[NH:14][C:13]([C:11]3[S:12][C:8]4[C:7]([N:22]5[CH2:23][CH2:24][O:25][CH2:26][CH2:27]5)=[CH:6][CH:5]=[C:4]([O:3][CH3:2])[C:9]=4[N:10]=3)=[N:21][C:16]=2[CH2:17]1)=[O:39])[CH3:42]

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 10928Ethyl chloroformate2×HCID 81531Diisopropylethylamine2×HCID 178492007HCID 178492007, compound

Product 1

HCID 178473319HCID 178473319, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.01 g 2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine hydrochloride in 0.8 ml tetrahydrofurane were added at 0–4° C. 0.06 ml N-ethyldiisopropylamine and 0.003 ml ethyl chloroformate in 0.26 ml tetrahydrofurane. The mixture was refluxed over night, additional 0.06 ml N-ethyldiisopropylamine and 0.05 ml ethyl chloroformate were added and heating was continued for 4 hours. 0.015 ml benzylamine were added and the mixture was kept at 80° C. for 1 hour. Silicagel was added and the solvent was distilled off. The residue was transferred to a column prefilled with silicagel and was chromatographed with ethylacetate. A second chromatography first with ethylacetate/hexane 1:1 and then with ethylacetate/methanol 9:1 yielded 0.003 g (25%) 2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid ethyl ester as yellow solid; MS (ISP): m/e=444 (M+H+).

Workup

  1. additionwere added at 0–4° C
  2. temperatureThe mixture was refluxed over night
  3. temperatureheating
  4. waitthe mixture was kept at 80° C. for 1 hour
  5. additionSilicagel was added
  6. distillationthe solvent was distilled off
  7. customwas chromatographed with ethylacetate

Sources & evidence

ORD record
ord-ac96fba0e28744a2a193d1d1e2a10d69
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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