1-(2-(1-Methylpyrrolidin-2-yl)ethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-amine → HCID 178480163, compound

HRID 1922443Notes

Reaction equation

HRID 1922443 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2[CH:16]=[C:17]([NH2:20])[CH:18]=[CH:19][C:10]1=2.CN(CCN1C2C(=CC=C([NH:44][C:45]([C:47]3[S:48][CH:49]=[CH:50][CH:51]=3)=N)C=2)CCC1)C(=O)OC1C=CC=CC=1>C(O)C.C([O-])(O)=O.[Na+]>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2[CH:16]=[C:17]([NH:20][C:45]([C:47]3[S:48][CH:49]=[CH:50][CH:51]=3)=[NH:44])[CH:18]=[CH:19][C:10]1=2

Participants

5

Reactant 2

HCID 674928321-(2-(1-Methylpyrrolidin-2-yl)ethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-amineHCID 178484202HCID 178484202, compound

Product 1

HCID 178480163HCID 178480163, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 4 (170 mg, 0.62 mmol) in dry ethanol (15 mL) was treated with 5 (0.355 g, 1.24 mmol) and stirred for overnight (17 h) at room temperature. The reaction mixture was diluted with saturated NaHCO3 solution (100 mL) and extracted with CH2Cl2 (2×50 mL). The combined organic fractions were washed with brine (50 mL), dried (Na2SO4) and concentrated. The crude product was purified by dry column chromatography (MeOH:CH2Cl2, 2:98 followed by 2 N NH3 in MeOH:CH2Cl2 3:97) to give compound 45 (177 mg, 74%) as a yellow solid. 1H-NMR (DMSO-d6) δ: 1.38-1.69 (m, 8H), 1.83-1.89 (m, 2H), 2.02-2.12 (m, 2H), 2.19 (s, 3H), 2.65-2.68 (m, 2H), 2.80-3.12 (m, 5H), 6.32 (brs, 2H), 6.62-6.64 (m, 2H), 6.85-6.88 (d, 1H, J=8.9 Hz), 7.06-7.09 (t, 1H, J=3.8 Hz), 7.56-7.58 (d, 1H, J=5.0 Hz), 7.69-7.71 (d, 1H, J=3.6 Hz); ESI-MS (m/z, %): 383 (MH+, 33), 192 (100), 142 (51). ESI-HRMS calculated for C22H30N4S (MH+), calculated: 383.2253; observed: 383.2263; HPLC-purity: 93.49% by area.

Workup

  1. extractionextracted with CH2Cl2 (2×50 mL)
  2. washThe combined organic fractions were washed with brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was purified
  6. dry with materialby dry column chromatography (MeOH:CH2Cl2, 2:98 followed by 2 N NH3 in MeOH:CH2Cl2 3:97)

Sources & evidence

ORD record
ord-042d6ae12273459baeda772d3de42165
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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