Methanol → HCID 86616742, compound

HRID 1678223Notes

Reaction equation

HRID 1678223 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([NH:22][C:23]5[CH:28]=[CH:27][N:26]=[C:25]([NH2:29])[N:24]=5)[CH:20]=4)[NH:15][N:14]=3)=[CH:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.C[OH:35]>C(Cl)Cl.C1COCC1>[C:3]([OH:2])(=[O:35])[CH3:12].[C:3]([OH:2])(=[O:35])[CH3:12].[NH2:29][C:25]1[N:24]=[C:23]([NH:22][C:19]2[CH:20]=[C:21]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[C:13]3[C:9]2[CH:10]=[C:11]3[C:6]([CH:5]=[CH:4][C:3]([OH:2])=[CH:12]3)=[CH:7][CH:8]=2)[CH:28]=[CH:27][N:26]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 59024090HCID 59024090, compound

Product 1

HCID 86616742HCID 86616742, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-[3-(7-methoxy-naphthalen-2-yl)-1H-indazol-5-ylamino]-pyrimidine-2-amine (Preparation #28 followed by general procedure N and F, 20 mg, 0.05 mmol) in CH2Cl2 (1 mL) was added 1M BBr3 in THF (1 mL). The mixture was stirred for about 2 hours at room temperature then methanol (1 mL) was added and the mixture concentrated under reduced pressure. The residue was purified by preparative reverse phase HPLC to give 7-[5-(2-amino-pyrimidin-4-ylamino)-1H-indazol-3-yl]-naphthalen-2-ol diacetate (12 mg, 60%); (DMSO-d6, 400 MHz) δ9.08 (s, 1H), 8.35 (s, 1H), 8.30 (s, 1H), 8.03 (d, 1H), 7.89 (d, 1H), 7.80 (m, 2H), 7.72 (d, 1H), 7.53 (d, 1H), 7.16 (s, 1H), 7.11 (d, 1H), 6.06 (bs, 2H), 5.99 (d, 1H), 1.87 (s, 6H); RP-HPLC (Table 1, Method e) Rt 1.43 min; m/z: (M+H)+ 369.2.

Workup

  1. concentrationthe mixture concentrated under reduced pressure
  2. customThe residue was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-0382dbcd9ee442aa9fa32a6a34f5e64c
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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