Dimethylamine, hydrochloride → HCID 67363002, compound

HRID 2046943Notes

Reaction equation

HRID 2046943 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@H:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH:22]=[N:23][N:24]([CH2:26][C:27]([OH:29])=O)[CH:25]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11].Cl.C[NH:32]C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@H:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH:22]=[N:23][N:24]([CH2:26][C:27]([NH2:32])=[O:29])[CH:25]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11]

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67365092HCID 67365092, compound

Product 1

HCID 67363002HCID 67363002, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (4-{3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyrazol-1-yl)-acetic acid (10.0 mg, 0.0231 mmol), dimethylamine hydrochloride (9.41 mg, 0.115 mmol), TBTU (14.8 mg, 0.0462 mmol), DIPEA (0.021 mL, 0.115 mmol) and DCM (3 mL) was stirred at rt for 30 min. The solution was concentrated in vacuo, redissolved in MeOH and purified via HPLC. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.89 (d, J=7.1 Hz, 3 H), 2.99 (s, 3 H), 3.14 (s, 3 H), 5.16 (s, 2 H), 5.29 (q, J=7.3 Hz, 1 H), 7.13-7.23 (m, 1 H), 7.38 (d, J=1.3 Hz, 1 H), 7.39-7.52 (m, 2 H), 7.63 (s, 1 H), 7.81 (s, 1 H), 8.34 (d, J=1.8 Hz, 1 H). MS (ES+): m/z 460.02 (100) [MH+]. HPLC: tR=3.26 min (ZQ3, polar—5 min).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionredissolved in MeOH
  3. custompurified via HPLC
  4. additionThe fractions containing the pure product
  5. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-279ba570df464fd19558b991ff5a863a
Source dataset
uspto-grants-2013_11
Patent number
US08592448B2

Reaction notes

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