Methanesulfonic Acid → HCID 86620138, compound

HRID 1664878Notes

Reaction equation

HRID 1664878 reaction equation
CS(O)(=O)=O.[F:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[C@H:14]1[CH2:20][N:19]2[C:21]([C:24](OC)([CH3:26])[CH3:25])=[CH:22][N:23]=[C:18]2[C@H:17]([NH:29]C(=O)OC(C)(C)C)[CH2:16][CH2:15]1.[N-:37]=[N+:38]=[N-:39].[Na+]>C(Cl)(Cl)Cl>[N:37]([C:24]([C:21]1[N:19]2[CH2:20][C@H:14]([C:8]3[CH:9]=[CH:10][CH:11]=[C:12]([F:13])[C:7]=3[F:6])[CH2:15][CH2:16][C@@H:17]([NH2:29])[C:18]2=[N:23][CH:22]=1)([CH3:25])[CH3:26])=[N+:38]=[N-:39]

Participants

5

Reactant 3

HCID 6395Methanesulfonic Acid2×HCID 33557Sodium AzideHCID 86620139HCID 86620139, compound

Product 1

HCID 86620138HCID 86620138, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methanesulfonic acid (0.30 mL, 4.63 mmol) was added to a solution of tert-butyl [(6S,9R)-6-(2,3-difluorophenyl)-3-(1-methoxy-1-methylethyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-yl]carbamate (50 mg, 0.115 mmol) and sodium azide (170 mg, 2.62 mmol) in chloroform (10 mL). After 1 h, additional methanesulfonic acid (0.95 mL, 14.65 mmol) was added. After 16 h, the reaction mixture was concentrated. Purification by reverse phase HPLC (100% water→100% acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (38 mg). MS 347.1 (M+1).

Workup

  1. waitAfter 16 h
  2. concentrationthe reaction mixture was concentrated
  3. customPurification by reverse phase HPLC (100% water→100% acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-c25c915f04494188bfe5f939636f933d
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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