Trifluoroacetic acid → 6-(2-Aminomethyl-pyrrolidin-1-yl)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid

HRID 519090Notes

Reaction equation

HRID 519090 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:15]=[C:16]2[C:25](=[CH:26][CH:27]=1)[O:24][CH2:23][C:22]1[N:17]2[CH:18]([CH3:37])[C:19](=[O:36])[N:20](COCC[Si](C)(C)C)[N:21]=1)(C)(C)C.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>C(Cl)Cl>[F:42][C:41]([F:44])([F:43])[C:39]([OH:45])=[O:40].[NH2:7][CH2:8][CH:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:15]=[C:16]2[C:25](=[CH:26][CH:27]=1)[O:24][CH2:23][C:22]1[N:17]2[CH:18]([CH3:37])[C:19](=[O:36])[NH:20][N:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727461{1-[4-Methyl-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-pyrrolidin-2-ylmethyl}-carbamic acid tert-butyl ester

Product 1

HCID 867274636-(2-Aminomethyl-pyrrolidin-1-yl)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of crude {1-[4-methyl-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-pyrrolidin-2-ylmethyl}-carbamic acid tert-butyl ester (0.117 mol) in DCM (2 mL) and TFA (1 mL) was stirred for 1 h at ambient temperature. The solvent was removed in vacuo and the residue was re-dissolved in MeOH (2 mL) and aqueous ammonium hydroxide (25%, 0.5 mL). The mixture was stirred for 2 h then purified by preparative HPLC (Table 3, Method 20) to give 6-(2-aminomethyl-pyrrolidin-1-yl)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid as white solid (0.0068 g, 13% for 2 steps). LC/MS (Table 1, Method 4) Rt=1.111 min; MS m/z: 316 [M+H]+

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was re-dissolved in MeOH (2 mL)
  3. stirringThe mixture was stirred for 2 h
  4. customthen purified by preparative HPLC (Table 3, Method 20)

Sources & evidence

ORD record
ord-2085e823731242fbbe76989fc44a7594
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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