Benzylamine → HCID 71555819, compound

HRID 706340Notes

Reaction equation

HRID 706340 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][CH2:6][C:7]1[C:15]2[C:10](=C[CH:12]=[CH:13][CH:14]=2)[NH:9]N=1.[NH2:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][NH2:20].C(Cl)(Cl)=S.[NH:29]1[C:37]2C(=CC=CC=2)C=N1.C(N)C1C=CC=CC=1>C1COCC1.CCOC(C)=O>[NH:29]1[C:37]2=[N:5][CH:6]=[CH:7][C:15]([CH2:10][NH:9][C:1]([NH:20][CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[NH2:16])=[S:2])=[C:14]2[CH:13]=[CH:12]1

Participants

8

Reactant 5

HCID 7504BenzylamineHCID 10040Thiophosgene2×HCID 1780962-(Aminomethyl)anilineHCID 131733696HCID 131733696, compoundHCID 178510685HCID 178510685, compound

Product 1

HCID 71555819HCID 71555819, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

Thiophosgene (115 uL, 1.50 mmol) was dissolved in THF (3 mL). In a separate vial, aminomethylazaindole (200 mg, 1.36 mmol) was dissolved in THF followed by the addition of TEA (228 uL, 1.20 mmol). The solution of compound 2 and TEA was then added to the vial containing thiophosgene. In another vial, 2-aminobenzylamine (199 mg, 1.63 mmol) and TEA (246 uL, 1.30 mmol) were dissolved in THF (2 mL). After the thiophosgene/azaindole mixture had been stirring for ˜15 minutes, the solution of benzylamine was added. After stirring overnight, EtOAc (2 mL) was added and the resulting solution was washed three times with water (5 mL). The solvent was then stripped and the crude product purified via normal phase chromatography (DCM/MeOH, 0%→15%) to give the product as a white solid.

Workup

  1. washthe resulting solution was washed three times with water (5 mL)
  2. customthe crude product purified via normal phase chromatography (DCM/MeOH, 0%→15%)

Sources & evidence

ORD record
ord-eeeb970bf8704814b28fc7eccf092969
Source dataset
uspto-grants-2015_11
Patent number
US09174984B2

Reaction notes

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