HCID 57906440, compound → HCID 57906603, compound

HRID 420497Notes

Reaction equation

HRID 420497 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[C:14]([Br:15])=[CH:13][N:12]=[C:11]([NH2:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].N1([CH:27](N(CCOC)C)[CH:28](N2C3C=CC=CC=3N=N2)[N:29]([CH2:31][CH2:32][O:33][CH3:34])[CH3:30])C2C=CC=CC=2N=N1>>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[C:14]([Br:15])=[CH:13][N:12]2[C:28]([N:29]([CH2:31][CH2:32][O:33][CH3:34])[CH3:30])=[CH:27][N:16]=[C:11]2[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 57906440HCID 57906440, compoundHCID 57906503HCID 57906503, compound

Product 1

HCID 57906603HCID 57906603, compoundYield 67%

Procedure

The cyclization was carried out as described for Example 6 from (2-amino-5-bromo-pyridin-4-ylmethyl)-carbamic acid tert-butyl ester (600 mg, 2.0 mmol, prepared according to Example 1, Step 1.3) and 1,2-bis-benzotriazol-1-yl-N,N′-bis-(2-methoxy-ethyl)-N,N′-dimethyl-ethane-1,2-diamine (871 mg, 2.0 mmol, prepared according to Example 6, Step 3.1). After the work-up, the crude was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME (containing 0.5% of a 7.0 M solution of NH3 in MeOH) 1:0→0:1) to yield the title compound (546 mg, 1.32 mmol, 67%) as a brownish oil. MS: 414 [M−1]+; HPLC: AtRet=1.40; TLC—RF 0.15 (hexane/DCM/TBME (containing 0.5% of a 7.0 M solution of NH3 in MeOH) 1:1:2).

Workup

  1. customAfter the work-up, the crude was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2
  2. washgradient elution, [hexane/DCM 1:1]/TBME (
  3. additioncontaining 0.5% of a 7.0 M solution of NH3 in MeOH) 1:0→0:1)

Sources & evidence

ORD record
ord-c64e5b3fbc784b3d93bcc47196bd194e
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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